[ CAS No. 3687-18-1 ] {[proInfo.proName]}

Name: 3687-18-1|3-Aminopropane-1-sulfonic acid|98%
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Quality Control of [ 3687-18-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3687-18-1 ]

SDS Specification

Alternatived Products of [ 3687-18-1 ]

Product Details of [ 3687-18-1 ]

CAS No. :	3687-18-1	MDL No. :	MFCD00008225
Formula :	C₃H₉NO₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SNKZJIOFVMKAOJ-UHFFFAOYSA-N
M.W :	139.17	Pubchem ID :	1646
Synonyms :	Tramiprosate;Homotaurine;Tramiprosate, Tramiprosate Na, Tramiprosate sodium, Alzhemed, Homotaurine, NC-758, NC 758, NC758;3-Sulfopropylamine;NSC 77071;NC 758;NC 531;Alzhemed	Chemical Name :	3-Aminopropane-1-sulfonic acid

Calculated chemistry of [ 3687-18-1 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	29.78
TPSA :	88.77 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-9.81 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-0.14
Log Po/w (XLOGP3) :	-3.75
Log Po/w (WLOGP) :	0.3
Log Po/w (MLOGP) :	-0.99
Log Po/w (SILICOS-IT) :	-1.18
Consensus Log Po/w :	-1.15

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	3.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	1.86
Solubility :	10000.0 mg/ml ; 72.0 mol/l
Class :	Highly soluble
Log S (Ali) :	2.48
Solubility :	41600.0 mg/ml ; 299.0 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.06
Solubility :	122.0 mg/ml ; 0.875 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.59

Safety of [ 3687-18-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3687-18-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 3687-18-1 ]
Downstream synthetic route of [ 3687-18-1 ]

[ 3687-18-1 ] Synthesis Path-Upstream 1~8

1
[ 107-57-3 ]
[ 3687-18-1 ]

Reference： [1] Patent: US4187245, 1980, A,

2
[ 1202497-71-9 ]
[ 3687-18-1 ]
[ 77693-74-4 ]

Reference： [1] Helvetica Chimica Acta, 2013, vol. 96, # 7, p. 1355 - 1365

3
[ 1120-71-4 ]
[ 3687-18-1 ]

Reference： [1] Journal of Organic Chemistry, 1961, vol. 26, p. 4841 - 4850

4
[ 1202497-71-9 ]
[ 3687-18-1 ]

Reference： [1] Synthesis (Germany), 2012, vol. 44, # 14, p. 2225 - 2230

5
[ 109-64-8 ]
[ 3687-18-1 ]

Reference： [1] Journal of Medicinal Chemistry, 1975, vol. 18, # 5, p. 502 - 505

6
[ 503-29-7 ]
[ 3687-18-1 ]

Reference： [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1937, vol. 204, p. 593[2] Bulletin de la Societe Chimique de France, 1938, vol. <5>5, p. 884

7
[ 5460-29-7 ]
[ 3687-18-1 ]

Reference： [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1937, vol. 204, p. 593[2] Bulletin de la Societe Chimique de France, 1938, vol. <5>5, p. 884

8
[ 56984-95-3 ]
[ 3687-18-1 ]

Reference： [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1937, vol. 204, p. 593[2] Bulletin de la Societe Chimique de France, 1938, vol. <5>5, p. 884

[ 3687-18-1 ] Synthesis Path-Downstream 1~88

1
[ 503-29-7 ]
[ 3687-18-1 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1937,vol. 204,p. 593
Bulletin de la Societe Chimique de France,1938,vol. <5>5,p. 884

2
[ 5460-29-7 ]
[ 3687-18-1 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1937,vol. 204,p. 593
Bulletin de la Societe Chimique de France,1938,vol. <5>5,p. 884

3
[ 56984-95-3 ]
[ 3687-18-1 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1937,vol. 204,p. 593
Bulletin de la Societe Chimique de France,1938,vol. <5>5,p. 884

4
[ 1120-71-4 ]
[ 3687-18-1 ]

Reference： [1]Journal of Organic Chemistry,1961,vol. 26,p. 4841 - 4850

5
[ 3687-18-1 ]
[ 22722-03-8 ]
[ 4919-01-1 ]

Reference： [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 502 - 505

6
3-Amino-propan-sulfonsaeure-⁽¹⁾-chlorid [ No CAS ]
[ 3687-18-1 ]

Reference： [1]Chemische Berichte,1963,vol. 96,p. 3068 - 3075

7
[ 109-64-8 ]
[ 3687-18-1 ]

Reference： [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 502 - 505

8
[ 75-15-0 ]
[ 3687-18-1 ]
[ 74-88-4 ]
Methyl(3-sulfopropyl)carbamodithioat [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1978,vol. 15,p. 981 - 985

9
[ 3687-18-1 ]
[ 65444-05-5 ]
[ 116112-33-5 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 602 - 608

10
[ 3687-18-1 ]
[ 19741-14-1 ]
[ 113811-47-5 ]

Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1326 - 1331

11
[ 75-15-0 ]
[ 3687-18-1 ]
[ 79-11-8 ]
3-(4-Oxo-2-thioxo-thiazolidin-3-yl)-propane-1-sulfonic acid [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1989,vol. 72,p. 17 - 28

12
[ 5264-35-7 ]
[ 3687-18-1 ]
[ 160427-73-6 ]

Reference： [1]Il Farmaco,1994,vol. 49,p. 653 - 658

13
[ 5693-62-9 ]
[ 3687-18-1 ]
[ 160427-74-7 ]

Reference： [1]Il Farmaco,1994,vol. 49,p. 653 - 658

14
[ 2525-16-8 ]
[ 3687-18-1 ]
[ 160427-75-8 ]

Reference： [1]Il Farmaco,1994,vol. 49,p. 653 - 658

15
3-Amino-propane-1-sulfonic acid hydroxyamide; hydrobromide [ No CAS ]
[ 3687-18-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1709 - 1714

16
3-Amino-propane-1-sulfonic acid hydroxy-methyl-amide; hydrobromide [ No CAS ]
[ 3687-18-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1709 - 1714

17
3-Amino-propane-1-sulfonic acid benzyl-hydroxy-amide; hydrobromide [ No CAS ]
[ 3687-18-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 1709 - 1714

18
[ 5554-48-3 ]
bromine water [ No CAS ]
[ 3687-18-1 ]

Reference： [1]Chemische Berichte,1890,vol. 23,p. 89

19
[ 5460-29-7 ]
[ 7732-18-5 ]
sodium sulfite [ No CAS ]
[ 3687-18-1 ]

Reference： [1]Bulletin de la Societe Chimique de France,1938,vol. <5>5,p. 871,875

20
[ 7647-01-0 ]
[ 6638-35-3 ]
bromine water [ No CAS ]
[ 3687-18-1 ]
3-(benzoylamino)propanesulphonic acid [ No CAS ]

Reference： [1]Chemische Berichte,1893,vol. 26,p. 1079

23
1.3-propanesultone [ No CAS ]
[ 3687-18-1 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1949,vol. 565,p. 22,28

24
2-mercapto-penthiazoline [ No CAS ]
[ 3687-18-1 ]

Reference： [1]Chemische Berichte,1890,vol. 23,p. 89

25
2-phenyl-1.3-thiazine dihydride [ No CAS ]
[ 3687-18-1 ]
3-(benzoylamino)propanesulphonic acid [ No CAS ]

Reference： [1]Chemische Berichte,1893,vol. 26,p. 1079

26
[ 3687-18-1 ]
[ 112433-86-0 ]
C₄⁽¹¹⁾CH₁₀NO₄S^(1-) [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. 643 - 651

27
[ 3687-18-1 ]
[ 501-53-1 ]
N-benzyloxycarbonyl-isothiazolidine 1,1-dioxide [ No CAS ]
benzyloxycarbonyl-homotauryl chloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 2642 - 2652

28
[ 3687-18-1 ]
[ 274679-00-4 ]
palladium bacteriochlorin 3¹-(3-sulfopropyl)amide dipotassium salt [ No CAS ]

Reference： [1]Photochemistry and Photobiology,2005,vol. 81,p. 983 - 993

29
palladium bacteriopheophorbide a 17³-(3-sulfo-1-oxy-succinimide)ester sodium salt [ No CAS ]
[ 3687-18-1 ]
palladium bacteriopheophorbide a 17³-(3-sulfopropyl)amide potassium salt [ No CAS ]

Reference： [1]Photochemistry and Photobiology,2005,vol. 81,p. 983 - 993

30
palladium bacteriopheophorbide a 17³-(3-sulfopropyl)amide potassium salt [ No CAS ]
[ 3687-18-1 ]
palladium bacteriochlorin 13¹,17³-di(3-sulfopropyl)amide dipotassium salt [ No CAS ]
palladium 3¹-(3-sulfopropylimino)bacteriochlorin 13¹,17³-di(3-sulfopropyl)amide tripotassium salt [ No CAS ]

Reference： [1]Photochemistry and Photobiology,2005,vol. 81,p. 983 - 993

31
palladium bacteriopheophorbide a 17^{3<sup/>-(3-sulfo-1-oxy-succinimide)ester sodium salt} [ No CAS ]
[ 3687-18-1 ]
palladium bacteriopheophorbide a 17^{3<sup/>-(3-sulfopropyl)amide potassium salt} [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
~ 80 - 90%	With dipotassium hydrogenphosphate; In water; dimethyl sulfoxide;pH 8.0;	Preparation of palladium bacteriopheophorbide a 173- (3-sulfopropyl) amide potassium salt (Compound 2 Ten (10) mg of compound 6 in 1 ml of DMSO was mixed with 20 mg of homotaurine (3-AMINO-1-PROPANE-SULFONIC acid) in 1 ml of 0.1 M K-phosphate buffer, pH 8.0 for overnight. Then the reaction mixture was partitioned in CHLOROFORM/WATER. The organic layer was dried over anhydrous sodium sulfate and evaporated. The dry residue was re-dissolved in chloroform-methanol (19: 1) and applied to a chromatographic column with silica. The product 7 was obtained with chloroform- methanol (4: 1) elution. The yield was about 80-90%. ESI-MS (-): 834 (M-K) m/z. NMR (MeOH-d4): 9.16 (5-H, s), 8.71 (10-H, s), 8.60 (20-H, s), 6.05 (132-H, s), 4. 51, 4. 39, 4.11, 3. 98 (7,8, 17,18-H, all M), 3.92 (134-ME, s), 3.48 (21-Me, s), 3.36 (121-Me, s), 3.09 (32-ME, s), 2.02-2. 42 (171 AND 1172-CH2, M), 2.15 (8L-CH2, q), 1.81 (71-ME, d), 1.72 (181-Me, d), 1.05 (82-ME, t), 3.04, 2.68, and 2.32 (CH2'S of homotaurine, M).

Reference： [1]Patent: WO2004/45492,2004,A2 .Location in patent: Page 26, 27

32
[ 3687-18-1 ]
[ 3282-30-2 ]
3-((2-2-dimethyl)propanoylamino)propanesulphonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%		3-amino-1-propanesulfonic acid (2.0 g, 14.4 mmol) was dissolved a NAOH (1.2 g, 30.2 mmol) solution in a mixture of 1, 4-dioxane (SmL) and water (15 mL). The mixture was cooled to 0C before pivaloyl chloride (2. 8 mL, 21.6 mmol) in 1,4-dioxane (5 mL) was added dropwise. The reaction mixture was allowed to warm up to room temperature and it was stirred at 65 C for 4h. The solvent was evaporated under reduced pressure. The resulting solid was dissolved in water (30 mL), and treated with Dowex 50WX8 resin. The suspension was stirred for 5 minutes and the resin was removed by filtration. The filtrate was evaporated under reduced pressure. The residual material was suspended in 20% ETOH/ACETONE. The mixture was stirres at reflux for 30 seconds. The solid product was collected by filtration, and dried in vacuo, to afford compound DT (1.3 g, 41%). 1H NMR (D20,500 MHz) 5 PPM 3. 16 (t, 2H, J= 6. 8 Hz), 2.75 (t, 2H, J= 7. 8 Hz), 1.78 (m, 2H), 1.1 (s, 9H). 13C NMR (D20, 125 MHz) 8 ppm 182. 75,48. 70,38. 57, 38. 18,26. 65,24. 27. ES-MS 222 (M-1).

Reference： [1]Patent: WO2004/113275,2004,A2 .Location in patent: Page 188; 189

33
[ 3687-18-1 ]
[ 622-78-6 ]
3-[(benzylamino)thiocarbonyl]amino-1-propanesulfonic acid sodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With sodium hydroxide; In water; at 70℃; for 1.5h;	3-AMINO-1-PROPANESULFONIC acid (1.07 g, 7.7 mmol) was dissolved in 1.5N NAOH (5.3 mL). To this solution was added benzyl isothiocyanate (1.02 ML, 7.7 mmol). The reaction mixture was stirred at 70C for 0. 5h ; a second-equivalent of benzyl isocyanate (1.02 ML, 7.7 mmol) was added. The reaction mixture was stirred for LH. The solvent was evaporated under reduced pressure. The residue was suspended in hot acetone. The solid material was collected by filtration, washed with hot acetone, and dried in vacuo. The residual material was recrystallized from MeOH (traces of water), affording compound AM, 1.00 g (42%).

Reference： [1]Patent: WO2004/113275,2004,A2 .Location in patent: Page 176

34
[ 3687-18-1 ]
[ 4411-25-0 ]
3-(N-1-adamantylcarbamyl)amino-1-propanesulfonic acid sodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With sodium hydroxide; In ethanol; water; at 70℃; for 1.5h;	3-AMINO-1-PROPANESULFONIC acid (1.06 g, 7.7 mmol) was dissolved in 1. 5N NAOH (5. 3 mL). To this solution was added 1-adamantyl isocyanate (1.36g 7.7 mmol) in hot EtOH (5 mL). The reaction mixture was stirred at 70C for 30min followed by addition (to the mixture) of one-equivalent of 1-adamantyl isocyanate (1.37, 7.7 mmol) in hot EtOH (5 mL). The reaction mixture was stirred for LH. The solvent was removed under reduced pressure. The residue was suspended in hot acetone. The solid material was collected by filtration, washed with hot acetone, and dried in vacuo. The solid was recrystallized from EtOH, affording compound AK, 519.4 mg (20%).

Reference： [1]Patent: WO2004/113275,2004,A2 .Location in patent: Page 175; 176

35
[ 3687-18-1 ]
[ 3173-56-6 ]
3-(N-benzylcarbamyl)amino-1-propanesulfonic acid sodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium hydroxide; In water; at 70℃; for 1.5h;	3-AMINO-1-PROPANESULFONIC acid (1.06 g, 7.7 mmol) was dissolved in 1. 5N NAOH (5. 3 mL). To this solution was added benzyl isocyanate (927 I1L, 7.7 mmol). The reaction mixture was stirred at 70C for 30 min, followed by addition to the mixture one-equivalent of benzyl isocyanate (927 UL, 7.7 mmol). The reaction mixture was stirred for LHOUR. THE solvent was evaporated under reduced pressure. The residue was suspended in hot acetone. The solid material was collected by filtration, washed with hot acetone, and dried in vacuo ; affording compound AH, 2.07 g (92%).

Reference： [1]Patent: WO2004/113275,2004,A2 .Location in patent: Page 175

36
[ 3687-18-1 ]
[ 1609-86-5 ]
C₈H₁₇N₂O₄S^(1-)*Na⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium hydroxide; In water; at 70℃; for 2h;	3-amino-1-propanesulfonic acid (2.0 g, 14.3 mmol) was dissolved in 1.6M NAOH (10 mL). To this solution was added tert-butyl isocyanate (1.1 g, 14.3 MMOL). The reaction mixture was stirred at 70C for lh, followed by addition of one equivalent of tert-butyl isocyanate (1.1 g, 14.3 mmol). The reaction mixture was stirred for LH. The solvent was evaporated under reduced pressure. The residue was suspended in EtOH (30 mL). The solid product was collected by filtration, washed with EtOH (20 mL) and acetone (20 mL). The resulting solid was dried in vacuo, to afford the sodium salt of compound DP (2.1 g, 66%). TH NMR (D20, 500 MHz) 8 ppm 3.03 (t, 2H, J= 6. 6 Hz), 2.76 (t, 2H, J= 7. 6 Hz), 1.72 (m, 2H), 1.12 (s, 9H). 13C NMR (DAL, 125 MHz) 8 PPM 160. 35,50. 26,48. 74,38. 31,28. 86,25. 24. ES-MS 280 (M+NA).

Reference： [1]Patent: WO2004/113275,2004,A2 .Location in patent: Page 187

37
[ 3687-18-1 ]
[ 103-80-0 ]
3-(phenylacetamido)-1-propanesulfonic acid sodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With sodium hydroxide; In water; at 0 - 20℃; for 22h;	3-AMINO-1-PROPANESULFONIC acid (1.0 g, 7.2 mmol) was dissolved in solution of 3M NAOH (7.2 mL). The mixture was cooled to 0C before phenylacetyl chloride (1.4 mL, 10.8 mmol) was added. The reaction mixture was allowed to warm up to room temperature and it was stirred for 22h. The solvent was evaporated under reduced pressure. The residue was suspended in 50% ETOH/ACETONE. The mixture was stirred at reflux for 30 sec. The solid material was collected by filtration and dried in vacuo. The product was recrystallized from 95 % ETOH/H2O and dried in vacuo. This allowed the isolation of compound AG, 880 mg (44%).

Reference： [1]Patent: WO2004/113275,2004,A2 .Location in patent: Page 174

38
[ 3687-18-1 ]
[ 71381-91-4 ]
3-[2-(4-isobutylphenyl)propanoyl]amino-1-propanesulfonic acid sodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%	With sodium hydroxide; In water; at 70℃;	Thionyl chloride (1.6 mL, 21.1 mmol) was added to ibuprofen (1.02 g, 4.9 mmol). The reaction mixture was heated to reflux for 4h. The solvent was evaporated, dried in vacuo, giving corresponding acid chloride. 3-AMINO-1-PROPANESULFONIC acid (308 mg, 2.2 mmol) was dissolved in 1. 5N NAOH (3 mL). To this solution was added dropwise the acid chloride (500.8 mg, 4.4 mmol, prepared above). The reaction mixture was stirred at 70C overnight. The solvent was removed under reduced pressure. The residue was suspended in acetone. The suspension was stirred at reflux for 30 seconds. The solid material was removed by filtration. The filtrate was evaporated to dryness under reduced pressure. The residual material was subjected to separation by flash chromatography (80% CH2CK/MEOH). This allowed the isolation of compound AL, 237 mg (14%).

Reference： [1]Patent: WO2004/113275,2004,A2 .Location in patent: Page 176

39
[ 3687-18-1 ]
[ 4202-38-4 ]
3-(N-N-dodecylcarbamyl)amino-1-propanesulfonic acid sodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium hydroxide; In water; at 70℃; for 1.5h;	3-amino-1-propanesulfonic acid (1.06 g, 7.7 mmol) was dissolved in 1. 5N NAOH (5. 3 mL). To this solution was added n-dodecyl isocyanate (1.7 mL, 7.7 mmol). The reaction mixture was stirred at 70C for 30min followed by addition to the mixture one- equivalent of n-dodecyl isocyanate (1.7 mL, 7.7 mmol). The reaction mixture was stirred for LH. The solvent was removed under reduced pressure. The residual material was suspended in hot acetone. The solid material was collected by filtration, washed with hot acetone, and dried in vacuo ; affording compound AJ, 2.47g (86%).

Reference： [1]Patent: WO2004/113275,2004,A2 .Location in patent: Page 175

40
[ 3687-18-1 ]
[ 3066-44-2 ]
3-(N-benzhydrylcarbamyl) amino-1-propanesulfonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%		The 3-amino-1-propanesulfonic acid (1.0 g, 7.2 mmol) was dissolved in 3N NAOH (370 mg, 9.4 mmol in 3 mL of water). After the solution was cooled to 0C, diphenylmethyl isocyanate (1.4 mL, 7.2 mmol) was added. The reaction mixture was allowed to warm up to room temperature, stirred for 8h (r. t. ), and followed by addition OF 3N NAOH (3 mL). The reaction mixture was stirred for 18H. The pH of the reaction mixture was brought to 3 with 5N EIC1. The solvent was evaporated under reduced pressure. EtOH (15 mL) was added and the mixture was stirred at reflux for 30 sec. The hot mixture was filtered. The filtrate was evaporated to dryness. This process was repeated 2 more times. The final product was dried in vacuo, affording compound AF, 837 MG (34%).

Reference： [1]Patent: WO2004/113275,2004,A2 .Location in patent: Page 173

41
[ 3687-18-1 ]
[ 30562-34-6 ]
C₃₁H₄₅N₃O₁₁S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dimethyl sulfoxide;	Compounds I in which Q1 is a sulfonic acid group (or compounds IV) can be synthesized by the reaction of a corresponding geldanamycin compound with a suitable aminosulfonic acid, as shown by procedure of Scheme 3 using 3-amino-1-propanesulfonic acid as an exemplar. The reaction can be performed in DMSO in the presence of a base such as triethylamine. The corresponding sulfonic acid compound derived from 2-amino-1-ethanesulfonic acid is disclosed in Schnur et al., J. Med. Chem. 38 (19), 3806-3812 (1995), the disclosure of which is incorporated herein by reference.

Reference： [1]Patent: US2005/267046,2005,A1 .Location in patent: Page/Page column 12; 13

42
[ 3687-18-1 ]
[ 170697-25-3 ]
[ 886540-57-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In water; acetone; at 15℃; for 0.166667h;pH 9.5;Heating / reflux;	A solution of 3,4-dicyanobenzenesulphonyl chloride (4.2 g, 0.018 mol, prepared by the method of Negrimovsky et al. Phosphorus, Sulfur, and Silicon 1995, 104, 161-167) in anhydrous acetone (20 ml) was added dropwise to a solution of 3-amino-1- propanesulphonic acid (5 g, 0.036 mol) in water (25 ml) at pH 9.5 (sat. aq. Na2CO3) at 150C (water bath). After completion of the addition the reaction mixture was heated under reflux for 10 min and allowed to cool down to room temperature. The solvent was removed under reduced pressure and a small amount of acetone/water (98:1) was added. The material was passed through a short pad of silica gel and the solvent was removed under reduced pressure. The resulting solid was crystallised from acetonitrile and hot filtered. The product was dried under vacuum over P2O5. Yield 3.8 g.

Reference： [1]Patent: WO2006/51258,2006,A1 .Location in patent: Page/Page column 8

43
[ 107-57-3 ]
[ 3687-18-1 ]

Yield	Reaction Conditions	Operation in experiment
	In water; ethylenediamine;	EXAMPLE 7 To a solution of ethylene diamine (30 g; 0.5 mole) in water (100 ml) was added 3-chloro-2-hydroxypropylsulfonic acid (98 g; 10.5 mole) in water (200 ml) and the mixture heated under reflux for 1 hour. Evaporation of the solvent yielded the aminopropyl sulfonic acid of the formula STR24 Analysis: Found N, 11.16; S, 14.81; Calculated N, 11.41; S, 16.2.

Reference： [1]Patent: US4187245,1980,A

44
[ 3687-18-1 ]
[ 3674-06-4 ]
[ 1034190-45-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In water; acetone; acetonitrile; at 20℃;	A solution of the N-hydroxysuccinimide ester of a N-Boc-protected amino acid or a carboxylic acid (48 mmol, 1.2 eq) in acetonitrile or acetone (50 mL) was added slowly to a solution of 3APS, 3-amino-1-propanesulfonic acid, 40 mmol, 1 eq in 2 N NaOH (sodium hydroxide, 23 mL, 1.2 eq). The reaction mixture was stirred at room temperature overnight. The mixture was evaporated to dryness. The residual material was stirred with Et2O (diethyl ether, 150 mL) at reflux for 1 h. After the mixture was cooled to room temperature, the solid material was filtered and dried in vacuo, and further purified according to one of the following work-up procedures

Reference： [1]Patent: US2008/146642,2008,A1 .Location in patent: Page/Page column 41-42

45
[ 3687-18-1 ]
[ 75-59-2 ]
[ 108-24-7 ]
[ 1131569-67-9 ]

Yield	Reaction Conditions	Operation in experiment
100%		Example 13; Synthesis of N-[3-(Chlorosulfonyl)propyl]acetamide (13)Step A: Tetramethylammonium N-acetylhomotaurate (13a)Tetramethylammonium N-acetylhomotaurate was synthesized adapting procedures disclosed in Durlach, U.S. Pat. No. 4,355,043 and U.S. Pat. No. 4,199,601, and DE 3019350. A 250 mL round bottomed flask equipped with a magnetic stir bar was charged with 3-amino-1-propanesulfonic acid (5.0 g, 36 mmol) and 20 mL of water. To the stirred solution, 13.0 g (36.0 mmol) of tetramethylammonium hydroxide ((CH3)4NOH, TMAH) (25 w-% in water) was added. The solution was stirred at room temperature for 1 hour and 4.1 mL of acetic anhydride (4.39 g, 43 mmol) was added. The mixture was stirred overnight at ca. 40 C. (oil bath) to ensure complete conversion. The resulting solution was extracted twice with 30 mL of diethyl ether or tert-butyl methyl ether (MTBE) and residual methanol in the aqueous phase was removed under reduced pressure using a rotary evaporator. The product was isolated from the residual water in the solution by lyophilization to yield 9.1 g (quant.) of the title compound (13a) as a colorless powder that was used without further purification after additional drying under high vacuum. 1H NMR (400 MHz, D2O): delta=1.88-1.95 (m, 2H), 1.97 (s, 3H), 2.88-2.92 (m, 2H), 3.16 (s, 12H), 3.27 (m, 2H) ppm. MS (ESI) m/z 180.04 (M-H)-.
100%		Tetramethylammonium N-acetylhomotaurate (1a) was synthesized adapting procedures disclosed in Durlach, U.S. Pat. No. 4,355,043, DE 3019350, and U.S. Pat. No. 4,199,601. A 250 mL round bottomed flask equipped with a magnetic stir bar was charged with 3-amino-1-propanesulfonic acid (5.0 g, 36.0 mmol) and 20 mL of water. To the stirred solution, 13.0 g (36.0 mmol) of tetramethylammonium hydroxide (25 w-% in water) was added. The solution was stirred at room temperature for 1 hour and acetic anhydride 4.1 mL (4.39 g, 43.0 mmol) was added. The mixture was stirred overnight at ca. 40 C. (oil bath) to ensure complete conversion. The resulting solution was extracted twice with 30 mL of diethyl ether or tert-butyl methyl ether (MTBE), and residual methanol in the aqueous phase was removed under reduced pressure using a rotary evaporator. The extract was isolated from the residual water in the solution by lyophilization to yield 9.1 g (quant.) of the title compound (1a) as a colorless powder that was used without further purification after additional thorough drying under high vacuum. 1H NMR (400 MHz, D2O): delta=1.88-1.95 (m, 2H), 1.97 (s, 3H), 2.88-2.92 (m, 2H), 3.16 (s, 12H), 3.27 (in, 2H) ppm. MS (ESI) m/z 180.04 (M-H)-.
100%		Tetramethylammonium N-acetylhomotaurate (1a) was synthesized adapting procedures disclosed in Durlach, U.S. Pat. No. 4,355,043, DE 3019350, and U.S. Pat. No. 4,199,601. A 250 mL round bottomed flask equipped with a magnetic stir bar was charged with 3-amino-1-propanesulfonic acid (5.0 g, 36.0 mmol) and 20 mL of water. To the stirred solution, 13.0 g (36.0 mmol) of tetramethylammonium hydroxide (25 w-% in water) was added. The solution was stirred at room temperature for 1 hour and acetic anhydride (4.1 mL, 4.39 g, 43.0 mmol) was added. The mixture was stirred overnight at ca. 40 C. (oil bath) to ensure complete conversion. The resulting solution was extracted twice with 30 mL of diethyl ether or tert-butyl methyl ether (MTBE) and residual methanol in the aqueous phase was removed under reduced pressure using a rotary evaporator. The extract was isolated from the residual water in the solution by lyophilization to yield 9.1 g (quant.) of the title compound (1a) as a colorless powder that was used without further purification after additional thorough drying under high vacuum. 1H NMR (400 MHz, D2O): delta=1.88-1.95 (m, 2H), 1.97 (s, 3H), 2.88-2.92 (m, 2H), 3.16 (s, 12H), 3.27 (m, 2H) ppm. MS (ESI) m/z 180.04 (M-H)-.

Reference： [1]Patent: US2009/82464,2009,A1 .Location in patent: Page/Page column 41
[2]Patent: US2009/69419,2009,A1 .Location in patent: Page/Page column 12; 43
[3]Patent: US2009/99253,2009,A1 .Location in patent: Page/Page column 37

46
[ 85-44-9 ]
[ 3687-18-1 ]
[ 127-08-2 ]
potassium 3‐(1,3‐dioxo‐2,3‐dihydro‐1H‐isoindol‐2‐yl)propane‐1‐sulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With acetic acid;	potassium 3-phthalimidopropane-1-sulfonate; Starting from 3-amino-1-propanesulfonic acid (3.0 g) this compound was prepared according to a procedure described for 3-phthalimidoethanesulfonylchloride in literature: Winterbottom, R.; Clapp, J., W.; Miller, W., H.; English, J., P.; Roblin, R., O. Studies in chemotherapy. XV. Amides of pantoyl turine. JACS, (1947), 1393-1401.Yield: 6.09 g (98%). 1H-NMR (D2O) delta (ppm) 7.74 (s, 4H), 3.71 (t, J= 6.9 Hz, 2H), 2.97-2.89 (m, 2H), 2.12-1.98 (m, 2H).

Reference： [1]Patent: EP2077263,2009,A1 .Location in patent: Page/Page column 13-14

47
[ 3687-18-1 ]
[ 82911-69-1 ]
[ 1189357-52-5 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 6126 - 6141

48
[ 3687-18-1 ]
[ 1218759-53-5 ]
[ 1229570-92-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; for 20h;Inert atmosphere; Reflux;	Example 23; Potassium diacetyl-/?/s-(N'4-3-aminopropane-sulfonate, N"4- methylthiosemicarbazone), KL9H2; To a stirring suspension of L1H2 (0.07 g, 0.3 mmol) in acetonitrile (7 ml_) was added 3-aminopropane-sulfonic acid (0.04 g, 0.3 mmol) and K2CO3 (0.04 g, 0.3 mmol). The resulting yellow suspension was heated at reflux for 20 h under an atmosphere of N2. The resulting white suspension was cooled to room temperature and the white solid was collected by filtration, washed with acetonitrile (x1 ) and diethyl ether (x3) and dried to give an impure white powder (0.09 g). 1H NMR (d6-DMSO, 500 MHz): £ 1.84, 2H, m, CH2-CH2-CH2; £ 2.18, 6H, s, CH3; £ 2.45, 2H, t, CH2-SO3K; £ 3.01 , 3H, d, NH-CH3; £3.64, 2H, m, NH-CH2; £8.21 , 1 H, br, NH; £8.51 , 1 H, br, NH.

Reference： [1]Patent: WO2010/66010,2010,A1 .Location in patent: Page/Page column 65

49
[ 3687-18-1 ]
[ 123-41-1 ]
[ 56769-36-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	In methanol; at 20℃; for 0.5h;	Preparation (2-hydroxyethyl)trimethylammonium 3-amino-1-propanesulfonate(choline homotaurinate). Procedure 1:At room temperature, homotaurine (69.6 g, 0.50 moles) was added in one portion to a stirred choline hydroxide solution (143 g of 45 wt.% solution in methanol, 0.53 moles of choline). An additional portion of methanol (50 ml.) was added to wash the inner wall of the flask. The mixture was stirred at room temperature for 30 min and a clear solution was obtained (note: in some cases, trace amounts of insoluble materials if any may be removed by filtration before the next step).The solution obtained was concentrated to dryness under reduced pressure (rotary evaporator) and the solid residual material was further dried at 70 C (water bath), to give a white solid (between 126 and 129 g).To the above solid was added isopropanol (300 mL), and the mixture obtained was heated (with effective stirring) to reflux to a clear solution. The solution was allowed to cool to room temperature. The mass of crystals formed was broken into slurry with a metal rod. The slurry was stirred in an ice-water bath for 0.5 to 1 hour. The crystalline solid was collected by filtration, washed with isopropanol (5 x 25 mL) and dried in a vacuum oven at 60 C overnight (or 24 to 72 hours), to give a white crystalline powder product, 110.5 to 111 g (91 to 92% yield): mp., 110-111 "C; 1H NMR (D2O, reference to DOH at 4.80 ppm) 1.87 (br-pent, 2H), 2.74 (br-t, 2H), 2.95 (br-t, 2H), 3.21 (s, 9H), 3.53 (br-m, 2H), 4.07 (br, 2H); ES-MS (m/z, positive mode) 104, 346; ES-MS (m/z, negative mode) 138, 380.

Reference： [1]Patent: WO2010/54485,2010,A1 .Location in patent: Page/Page column 25-26

50
[ 3687-18-1 ]
[ 406-76-8 ]
L-carnitine 3-amino-1-propanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water;	Preparation of the organic nutrient salt of carnitine and homotaurine: L-camitine inner salt (10.6 g, 0.066 mole) was dissolved in water (15 ml.) with brief heating. To the solution was added homotaurine (9.16, 0.066 mole) with constant stirring.More water (10 mL) was added to give a clear solution. Solvent was evaporated under reduced pressure. The residual solid was suspended in isobutanol (30 mL); and the mixture was concentrated to dryness under reduced pressure. The isobutanol treatment was repeated with a second portion of 15 mL isobutanol. The residual material (18.0 g) was suspended in acetone (200 mL) and the mixture was stirred overnight at room temperature.The solid material was collected by filtration, dried at 60 C under vacuum, giving a white crystalline powder (17.8 g). 1H-NMR spectrum of the product was recorded in D2O (seeFigure 1).

Reference： [1]Patent: WO2010/54485,2010,A1 .Location in patent: Page/Page column 25

51
[ 3687-18-1 ]
[ 1234423-98-3 ]
[ 76-05-1 ]
[ 1234363-98-4 ]

Yield	Reaction Conditions	Operation in experiment
4%		Into a 50-mL round-bottom flask, was placed a solution of 3-aminopropane-l -sulfonic acid (180 mg, 1 29 mmol, 1 00 equiv) in tetrahydrofiiran/water (10/10 niL) with sodium bicarbonate (430 mg, 5 12 mmol) This was followed by the addition of 3-(6, 8-dichloro-2-methyl-l, 2,3,4- tetrahydroisoquinohn-4 yl)benzene-l-sulfonyl chlonde (500 mg, 1 29 mmol, 099 equiv) in several batches The resulting solution was stirred for 4 h at room temperature The reaction progress was monitored by LCMS The pH value of the solution was adjusted to 6 with IM hydrogen chlonde The resulting mixture was concentrated under vacuum The crude product (500 mg) was purified by preparative HPLC to give 26 7 mg of the title compound (4%) as a TFA salt 1H-NMR (300MHz, DMSO, pprri) 10 28(s, IH), 7 53-7 79(m, 6H), 6 83(s, IH), 4 74(s, 2H), 4 51(s, IH), 3 90(s, IH), 3 06 (s, 3H), 2 86-2 93(m, 2H), 2 33-2 44(m, 2H), 1 58-1 63(m, 2H) MS (ES, m/z) 493 [M+H]+.

Reference： [1]Patent: WO2010/78449,2010,A2 .Location in patent: Page/Page column 157

52
[ 85-44-9 ]
[ 3687-18-1 ]
potassium 3‐(1,3‐dioxo‐2,3‐dihydro‐1H‐isoindol‐2‐yl)propane‐1‐sulfonate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 2390 - 2400

53
[ 3687-18-1 ]
[ 1242284-19-0 ]
C₃₄H₂₄N₆O₁₀S₂^(2-)*2Li⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With lithium hydroxide; In water;pH 9.3 - 9.9;	Synthesis of Compound 8: 3-amino-l -propane sulfonic acid (36.9 mmol, 5.14 g) was dissolved in 100 mL of water. The solution was brought to pH 9.9 with 18 mL of 1 M LiOH. The bis-acid chloride (Compound 6) was added to the solution and the mixture stirred for 3 hours. Another 7 mL of IM LiOH was added to raise the pH from 8.8 to 9.4 and the mixture continued stirring overnight. The pH dropped to 1.6 overnight. Another 18 mL of 1 M LiOH was added to raise the pH to 9.3, and the mixture stirred for 2 more hours. The pH was adjusted to 2.5 with IM HCl, and the solids were removed by filtration. Excess salts were removed via a RO membrane, and the solution concentrated under vacuum to 7.5 wt%. Yield (4.9 g as solid, 70%). LCMS (M-H = 741).

Reference： [1]Patent: WO2010/99223,2010,A1 .Location in patent: Page/Page column 30

54
[ 3687-18-1 ]
[ 220015-49-6 ]
[ 121-44-8 ]
[ 1353868-79-7 ]

Reference： [1]Organometallics,2012,vol. 31,p. 729 - 738

55
[ 3687-18-1 ]
[ 98-88-4 ]
3-(benzoylamino)propanesulphonic acid [ No CAS ]

Reference： [1]Biopharmaceutics and Drug Disposition,2011,vol. 32,p. 343 - 354

56
[ 3687-18-1 ]
[ 38565-52-5 ]
[ 1262880-20-5 ]

Yield	Reaction Conditions	Operation in experiment
		100 ml glass flask was charged with 0.84 g of lithium hydroxide monohydrate (manufactured by Wako Pure Chemical Industries, Ltd.), 18.21 g of ion exchanged water, 18.21 g of isopropyl alcohol, and 2.87 g (0.02 mol) of 3-aminopropanesulfonic acid (Sigma-Aldrich Japan), and the mixture was heated to 78C. To this mixture, 15.34 g (0.04 mol) of the compound (3-1) was added dropwise for 2 hours, and the reaction was allowed to proceed for 24 hours to obtain a water / isopropyl alcohol solution containing 33.7% of the reaction product mainly comprising the compound (1-7). The reaction solution was analyzed by gas chromatography, and conversion rate of the compound (3-1) was 99.1%. To confirm the identity of the reaction product, a portion of the reaction solution was dried at 110C for 2 hours, and the resulting solid was analyzed by NMR. 1H-NMR and 13C-NMR spectrum data for the compound (1-7) were as shown below. 1H-NMR (300 MHz, solvent: CD3OD, standard substance: hexamethyldisiloxane), ? (ppm) : 1.8 to 1.9 (2H), 2.0 to 2.4 (2H), 2.4 to 2.8 (10H), 4.0 to 4.1 (2H) 13C-NMR (300 MHz, solvent: CD3OD standard substance: hexamethyldisiloxane) ? (ppm): 23.2, 36.4 to 37.0 (t), 50.3, 55.4, 55.7, 62.1, 63.0, 63.8, 64.8 The gas chromatographic analysis and the NMR spectrum data indicated substantial absence of the non-reacted compound (3-1), namely, that most of the compound (3-1) had been converted to the intended product.

Reference： [1]Patent: EP2460790,2012,A1 .Location in patent: Page/Page column 10

57
[ 3687-18-1 ]
[ 38565-52-5 ]
[ 1262880-14-7 ]

Yield	Reaction Conditions	Operation in experiment
		100 ml glass container was charged with 0.80 g of sodium hydroxide, 18.2 g of ion exchanged water, 18.2 g of isopropyl alcohol, and 2.87 g (0.02 mol) of 3-aminopropanesulfonic acid (manufactured by Sigma-Aldrich Japan), and the mixture was heated to the reflux temperature. To this mixture, 15.33 g (0.04 mol) of the compound (3-1) was added dropwise for 2.5 hours, and the reaction was allowed to proceed for 36 hours to obtain a water / isopropyl alcohol solution containing 32.7% of the reaction product mainly comprising the compound (1-5). The reaction solution was analyzed by gas chromatography, and conversion rate of the compound (3-1) was 99.6%. To confirm the identity of the reaction product, a portion of the reaction solution was dried at 110C for 2 hours, and the resulting solid was analyzed by NMR. 1H-NMR and 13C-NMR spectrum data for the compound (1-5) were as shown below. 1H-NMR (300 MHz, solvent: CD3OD standard substance: hexamethyldisiloxane) ? (ppm) : 1.8 to 1.9 (2H), 2.0 to 2.4 (2H), 2.4 to 2.8 (10H), 4.0 to 4.1 (2H) 13C-NMR (300 MHz, solvent: CD3OD standard substance: hexamethyldisiloxane) ? (ppm): 23.2, 36.4 to 37.0 (t), 50.3, 55.4, 55.7, 62.1, 63.0, 63.8, 64.8 The gas chromatographic analysis and the NMR spectrum data indicated substantial absence of the non-reacted compound (3-1), namely, that most of the compound (3-1) had been converted to the intended product.

Reference： [1]Patent: EP2460790,2012,A1 .Location in patent: Page/Page column 10

58
[ 1202497-71-9 ]
[ 3687-18-1 ]

Reference： [1]Synthesis,2012,vol. 44,p. 2225 - 2230

59
[ 3687-18-1 ]
[ 1444121-74-7 ]
C₂₂H₃₀ClN₉O₅S*2ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%		A mixture of acid example 1 .51 (360 mg; 0.427 mmol), BOC-anhydride (247 mg; 1 .13 mmol) and triethylamin (230 muIota; 1.17 mmol) in THF (100 ml) is stirred at 60 C for 3d. Volatiles are evaporated and the crude BOC-protected intermediate is further reacted without purification as follows: A mixture of the intermediate, triethylamine (170 muIota; 1 .23 mmol) and HATU (147 mg; 0.387 mmol) in DMF (6 ml) and ACN (6 ml) is stirred at ambient temperature for 30 min. The amino component 3-Amino-propylsulphonic acid (98 mg; 0.702 mmol) is added and the mixture is stirred overnight. The mixture is evaporated and the residue is purified by RP-HPLC (modifier: TFA) to yield the BOC-protected amide intermediate which is taken up in DCM and TFA and stirred overnight. Volatiles are evaporated and the residue is taken up in HCl in methanol and evaporated again. The latter is repeated for further two times to yield the title compound. Yield: 31 mg (15% of theory) C22H30ClN9O5S x 2 HCl. ESI Mass spectrum: m/z = 568 [M+H]+; m/z = 566 [M-H]-. RP-HPLC: Rt = 0.93 min (HPLC method 7).
		Example 2.1 A mixture of acid example 1.51 (360 mg; 0.427 mmol), BOC-anhydride (247 mg; 1.13 mmol) and triethylamine (230 mul; 1.17 mmol) in THF (100 ml) is stirred at 60 C. for 3d. Volatiles are evaporated and the crude BOC-protected intermediate is further reacted without purification as follows: A mixture of the intermediate, triethylamine (170 mul; 1.23 mmol) and HATU (147 mg; 0.387 mmol) in DMF (6 ml) and ACN (6 ml) is stirred at ambient temperature for 30 min. The amino component 3-Amino-propylsulphonic acid (98 mg; 0.702 mmol) is added and the mixture is stirred overnight. The mixture is evaporated and the residue is purified by RP-HPLC (modifier: TFA) to yield the BOC-protected amide intermediate which is taken up in DCM and TFA and stirred overnight. Volatiles are evaporated and the residue is taken up in HCl in methanol and evaporated again. The latter is repeated for further two times to yield the title compound. Yield: 31 mg (15% of theory) C22H30ClN9O5S*2HCl ESI Mass spectrum: m/z=568 [M+H]+; m/z=566 [M-H]-

Reference： [1]Patent: WO2013/92674,2013,A1 .Location in patent: Page/Page column 66; 67
[2]Patent: US2013/157981,2013,A1 .Location in patent: Paragraph 0492; 0493; 0494; 0495; 0496; 0497

60
[ 1202497-71-9 ]
[ 3687-18-1 ]
[ 77693-74-4 ]

Reference： [1]Helvetica Chimica Acta,2013,vol. 96,p. 1355 - 1365

61
[ 3687-18-1 ]
C₂₈H₂₄O₈ [ No CAS ]
15-deacetyl-13-5-amino-1-propanesulfonic acid-hypocrellin B [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With sodium hydroxide; In N,N-dimethyl-formamide; at 125℃; for 3h;Darkness;	General procedure: 2 (50mg, 0.095m mol) in DMF (10mL) was mixed with 3-amino-1-propane-sulfonic acid (500mg, 3.60m mol) in the presence of solid sodium hydroxide (100mg, 2.50mmol) and allowed to react at 125C in dark for 3h. Evaporated under vacuum to get rid of the solvent, the dark brown solid residue was obtained and applied to a 1% citric acid-silica gel column with dichloromethane:methyl alcohol:acetic acid=250:50:1(v/v/v) as the eluant. The brown-black constituent was collected and applied to 1% citric acid-silica gel plate with ethyl acetate:methyl alcohol=3:1 (v/v) used as the eluant. C-18 reversed phase column chromatography was used for the further purification of 3 with methanol:water=6:4 used as the eluant. The grey-brown constituent was the derivative in a yield of 36%, characterized as below. UV-vis (DMSO, lambdamax, log epsilon): 459nm (4.27), 580nm (4.29), 635nm (4.22); IR (KBr, numax, cm-1): 3444, 3363, 2935, 1610; 1H NMR (400MHz, D2O, delta): 6.50, 6.45 (s, 2H, 5,8-H), 6.11 (s, 1H, 15-H), 5.85 (s, 1H, 13-H), 4.18, 4.14, 4.10, 4.07 (m, 12H, 2,6,7,11-OCH3), 3.82 (m, 2H, 17-CH2), 3.15 (m, 2H, 19-CH2), 2.73 (s, 3H, 16-CH3), 2.43-2.45 (m, 2H, 18-CH2); 13C NMR (100MHz, CDCl3, delta): 185.52, 185.48, 168.02, 167.68, 164.60, 163.17, 149.23, 146.44, 144.48, 134.17, 134.00, 133.77, 123.89, 123.77, 123.72, 122.92, 121.68, 120.84, 108.37, 107.12, 102.91, 102.84, 61.01, 60.81, 43.63, 31.27, 30.80, 20.43, 18.12; ESI-MS (m/z): 622.2 (M-1). Anal. Calcd for C31H29NO11S: C, 59.70; H, 4.69; N, 2.25; S, 5.14; Found: C, 59.49; H, 4.98; N, 2.05; S, 4.79. HPLC (methanol/water=8:2): retention time: 10.064min.

Reference： [1]Dyes and Pigments,2013,vol. 99,p. 930 - 939

62
[ 3687-18-1 ]
C₁₀H₁₃N₂O₈P^(2-)*2C₆H₁₅N [ No CAS ]
thymidine-5′-(3-aminopropanesulfonic acid) phosphoramidate di(triethylammonium) salt [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 3950 - 3962

63
[ 3687-18-1 ]
C₆₉H₇₇EuN₇O₁₇P₃ [ No CAS ]
C₇₅H₉₂⁽¹⁵³⁾EuN₁₀O₂₃P₃S₃ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 10718 - 10722
Angew. Chem.,2014,vol. 126,p. 10894 - 10898,5

64
[ 3687-18-1 ]
[ 40846-94-4 ]
C₁₁H₂₁NO₄S₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With sodium hydrogencarbonate; In water; N,N-dimethyl-formamide; at 0 - 25℃; for 18h;	To a suspension of 3-aminopropan-1-sulfonic acid (homotaurine) (1.5 g, 10.88 mmol)and NaHCO3 in H20/DMF (1:1 v/v, 30 mL) is added at 0 C a solution of compound Iin DMF (20 mL). The mixture is heated at room temperature (20-25 C) and stirred for18 hours. After several washings with AcOEt, the acqueous phase is evaporated and the yellow solid is dissolved in methanol and filtered over silica gel (dichloromethane/methanol 2:1). This way, compound 2 is obtained as a pure solid with a 59% yield.1H NMR (D20): d 1.20-1.25 (m), 1.4-1.6 (m), 1.65-1.85 (m), 2.05 (t), 2.2-2.4 (m), 2.6-2.8 (m), 3.0-3.2 (m), 3.4-3.6 (m), 7.8 (bs).

Reference： [1]Patent: WO2015/128697,2015,A1 .Location in patent: Page/Page column 9

65
[ 3687-18-1 ]
C₆₃H₅₇EuN₆O₁₅*3H₃N [ No CAS ]
ammonium bicarbonate [ No CAS ]
C₇₂H₇₈EuN₉O₂₁S₃*3H₃N [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 570 - 580

66
[ 3687-18-1 ]
C₆₃H₆₆EuN₆O₁₅P₃*3H₃N [ No CAS ]
C₇₂H₈₇EuN₉O₂₁P₃S₃*3H₃N [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 570 - 580

67
[ 3687-18-1 ]
C₆₄H₇₁EuN₇O₁₃P₃ [ No CAS ]
C₆₇H₇₈EuN₈O₁₅P₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In water; N,N-dimethyl-formamide; at 20℃; for 16h;Inert atmosphere;	Benzotriazol-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate (0.2 mg, 0.37 mumol) and diisopropylethylamine (0.11 muL, 0.65 mumol) were added to a solution of complex 70c (0.35 mg, 0.25 mumol) in dimethylformamide (50 muL). The mixture was stirred at room temperature for 5 min. A solution of homotaurine (0.05 mg, 0.37 mumol) in water (10 muL) was added to this solution, and then the solution was stirred at room temperature under inert atmosphere for 16 h. The progress of the reaction was monitored by LC-MS. After this time, reaction was complete. The solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (95 muL) under inert atmosphere at 4 C. and trifluoroacetic acid was added to this solution. The mixture was stirred for 20 min and then the solvent was removed under reduced pressure. The reaction mixture was purified by semipreparative HPLC to give compound 93 (0.3 mg, 85%). HRMS (ESI-) calculated for C62H69EuN8O13P3S [M]-, m/z 1409.3120 found: 1409.3110.

Reference： [1]Patent: US2015/361116,2015,A1 .Location in patent: Paragraph 0387

68
[ 3687-18-1 ]
C₆₆H₇₁EuN₇O₁₇P₃ [ No CAS ]
C₇₅H₉₂EuN₁₀O₂₃P₃S₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20℃; for 1h;Inert atmosphere;	<strong>[3687-18-1]Homotaurin</strong>e (4.0 mg, 28.8 mumol), (O-(7-azabenzotriazol-1-yl)-N,N,N?,N?-tetramethyluronium hexafluorophosphate) (5.4 mg, 14.4 mumol) and diisopropylethylamine (9 muL, 48 mumol) were added successively to a solution of compound 113 (7.1 mg, 4.8 mumol) in anhydrous dimethylsulfoxide (1 mL). The mixture was stirred at room temperature for 1 h under inert atmosphere. The crude product was purified by preparative HPLC to give compound 114 in the form of a white solid (6.6 mg, 70%); HRMS (ESI+) calculated for C75H94N10O23P3S3Eu [M+2H]2+, m/z 922.2040 found: 922.2045.

Reference： [1]Patent: US2015/361116,2015,A1 .Location in patent: Paragraph 0437

69
[ 3687-18-1 ]
[ 149457-83-0 ]
C₃₁H₂₉NO₁₁S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With sodium hydroxide; In 1,4-dioxane; at 100℃; for 4h;Inert atmosphere;	HypocrellinB (HB) 150mg (2.8X10 4 mol), 3-amino-1-propanesulfonicacid 1500mg(1.1X103mol) with solid sodium hydroxide1040mg (9. 8X103 moles) added into 20ml 1,4- dioxane, After thorough mixing, under a Argongas atmosphere the reaction was heated to 100 C and Mechanical stirring for 3 hours. Aftercompletion of the reaction, the solvent drained under reduced pressure, the suitableamount of deionized water was used to dissolve the residue, and then added withan equal amount of deionized water and ethyl acetate was used for extractionand extracted six times, after water layer was drained of , by chromatographicmethods carried out separation, first with dichloromethane, methanol and aceticacid with a volume ratio of 125: 25: 1 mixture and the obtained mixture wassubjected to expansion. The collected Brown product composition Rf value is 0.5, and then the brown product composition Rf value of 0.5 with ethyl acetate andmethanol with volume ratio of 3: 1mixture and obtained expanded solution was subjected to expansion, The collected gray-blackproduct composition Rf value is 0.4,obtained present invention provided formulaI represents 15 position deacetylation13 position 3-amino-1-propanesulfonic acid substituted Hypocrellinderivatives (n=3) 61mg, yield 35%.

Reference： [1]Patent: CN101948412,2016,B .Location in patent: Paragraph 0061; 0062

70
[ 3687-18-1 ]
hypocrellin A [ No CAS ]
C₃₁H₃₁NO₁₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With sodium hydroxide; In acetonitrile; at 80℃; for 2h;Inert atmosphere;	Hypocrellin A (HA) 100mg (1.8X104mol), 3-amino-1-propanesulfonic acid1200mg(8.6X103mol) with solid sodium hydroxide300mg (5. 4X10 3moles) added into 20ml of acetonitrile, After thorough mixing, under a Argongas atmosphere the reaction was heated to 80 C and Mechanical stirring for 2 hours. Aftercompletion of the reaction, the solvent drained under reduced pressure, the suitableamount of deionized water was used to dissolve the residue, and then added withan equal amount of deionized water and ethyl acetate was used for extractionand extracted four times, after water layer was drained of , by chromatographicmethods carried out separation, first with dichloromethane, methanol and aceticacid with a volume ratio of 250: 50: 1 mixture and the obtained mixture wassubjected to expansion. The collected Brown product composition Rf value is 0.5, and then the brown product composition Rf value of 0.5 with ethyl acetate andmethanol with volume ratio of 3: 1mixture and obtained expanded solution was subjected to expansion, The collected gray-blackproduct composition Rf value is 0.4,obtained present invention provided formulaI represents 15 position deacetylation13 position 3-amino-1-propanesulfonic acid substituted Hypocrellinderivatives (n=3) 40mg, yield 36%.

Reference： [1]Patent: CN101948412,2016,B .Location in patent: Paragraph 0050; 0051

71
[ 3687-18-1 ]
[ 5453-04-3 ]
C₃₆H₄₂N₂O₁₂S₂^(2-)*2K⁽¹⁺⁾ [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1185 - 1190

72
[ 3687-18-1 ]
[ 24424-99-5 ]
[2-(tert-butyloxycarbonylamino)ethyl]methanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; triethylamine; In dichloromethane; at 0℃;	At 0 C, 1.39 g of a compound of formula a, 27.9 mL of triethylamine, 26.2 g of di-tert-butyl dicarbonate (BOC) 2O and 1.2 g of 4-dimethylaminopyridine was added 150 mL of dichloromethane, stirred, and after completion of the reaction, Washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, Filtering and concentrating to obtain a compound of formula b;

Reference： [1]Patent: CN104478798,2017,B .Location in patent: Paragraph 0040-0043

73
[ 3687-18-1 ]
[ 21431-12-9 ]
C₁₁H₁₃N₂O₅S₃^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In N,N-dimethyl-formamide; at 20℃;	Example 4 (0066) Preparation of Compound (34) (0067) (0068) 1 g (4 mmol) of compound 33 was dissolved in 5 mL DMF C. 835 mg (6 mmol) of 3-aminopropanesulfonic acid was added, followed by addition of triethylamine (1.4 mL, 10 mmol). The reaction mixture was stirred at room temperature until TLC shows the reaction is complete. Ethyl acetate (40 mL) was added to the stirring mixture. The resulting precipitate was collected by filtration, and washed with ethyl acetate, and dried under high vacuum to give compound 34.
	With triethylamine; In N,N-dimethyl-formamide; at 20℃;	1 g (4 mmol) of compound 33 was dissolved in 5 mL of DMF, and 835 mg (6 mmol) of 3-aminopropanesulfonic acid was added.Triethylamine (1.4 mL, 10 mmol) was then added.The reaction mixture was stirred at room temperature until TLC showed the reaction was completed.Ethyl acetate (40 mL) was added to the stirred mixture.The resulting precipitate was collected by filtration and washed with ethyl acetate.Drying under high vacuum gave compound 34.

Reference： [1]Patent: US9850382,2017,B1 .Location in patent: Page/Page column 20
[2]Patent: CN108440987,2018,A .Location in patent: Paragraph 0072-0075

74
[ 3687-18-1 ]
(S)-4-(1-(6-(2-((4-cyanophenethyl)carbamoyl)azetidin-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl)piperidin-4-yl)butanoic acid [ No CAS ]
(S)-3-(4-(1-(6-(2-((4-cyanophenethyl)carbamoyl)azetidin-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl)piperidin-4-yl)butanamido)propane-1-sulfonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	To a solution of Compound 28 (530 mg, 0.97 mmol) in DCM (7 mL) were added sequentially l-ethyl-3-(3-dimethylaminopropyl)carbodiimide (224 mg, 1.17 mmol), N- hydroxybenzotriazole (145 mg, 1.07 mmol), taurine (128 mg, 1.02 mmol) and diisopropylethylamine (0.43 mL, 2.5 mmol). The reaction mixture was stirred at room temperature overnight, and the solvent was evaporated in vacuo. The residue was purified by column chromatography (reverse phase C-18 column, 0-42% aceonitrile/ water containing 0.25% formic acid) and then further purified by MS-HPLC to afford Compound 56 (270 mg, 43%). LCMS (method A): m/z 652.6 (M+H)+. XH NMR (CD3OD) delta 7.59 (d, 2H), 7.37 (d, 2H), 4.49 (br s, 1H), 4.37 (t, 2H), 3.62 (t, 3H), 3.50-3.34 (m, 3H), 3.00-2.83 (m, 6H), 2.30 (m, 2H), 2.18 (m, 1H), 2.01 (m, 3H), 1.82 (d, 2H), 1.60 (t, 3H), 1.18 (m, 2H); Using the procedure as described in Example 7 and using DMF as solvent, (1383) Compound 231 (80 mg, 0.15 mmol) was converted to Compound 248 (20 mg, 20%). LCMS (Method A): m/z 666.7 (M+H)+. 'H NMR (DMSO-d6) delta 8.20 (m, IH), 7.83-7.80 (m, IH), 7.70-7.68 (m, 2H), 7.40-7.38 (m, 2H), 5.57 (s, IH), 4.60-4.57 (dd, IH), 4.29-4.23 (m, 2H), 3.98-3.68 (m, 4H), 3.39-3.33 (m, 2H), 3.09-3.04 (m, 2H), 3.25-2.79 (m, 4H), 2.46-2.38 (m, 2H), 2.18-2.13 (m, IH), 2.04-2.01 (m, 2H), 1.73-1.63 (m, 4H), 1.55-1.47 (m, 3H), 1.20-1.14 (m, 2H), 1.04-0.94 (m, 2H).

Reference： [1]Patent: WO2018/5794,2018,A2 .Location in patent: Page/Page column 119-120; 206-207

75
[ 3687-18-1 ]
4-[(1S,4S,5R)-5-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy}-2-azabicyclo[2.2.1]heptan-2-yl]benzoic acid [ No CAS ]
2-({4-[(1S_.4S,5R)-5-[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy}-2-azabicyclo[2.2.1]heptan-2-yl]phenyl}formamido)ethane-1-sulfonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 80℃; for 3h;	To a 50 mL round-bottom flask '.vas added 4-[(lS,4S,5R)-5-[[5-cydopropyl-3-(2,6-25 dichorophenyl)-1 ,2-oxazol-4-yllmethoxy ]-2-azabicydo[2.2.l]hepta.n-2-y l]benzoic acid I-52(200 mg, 0.40 rnmol, LOO equiv.), DIEA (206 mg, 1.59 mmol, 4.00 equiv.), N,Ndimethyltormamide(10 mL), PyBOP (312 mg, 1.30 equiv.), and 3-aminopropane-1-sulfonicacid (75 mg, 0.54 mmol, 1.50 equiv.). The resulting mixture was heated at 80C for Jh withsiirreing. After cooling to room temperature, the mixture was diluted with 100 mL ofEA, washed with brine (50 mL x 2), dried over anhydrous sodium sulfate and concentrated undervacuurn. 1l1e crude product was purified by Prep-HPLC using the following conditions:Column, XBridge Prep C18 OBD Column, l9jA150mm Sum .SumC-0013: mobile phase,Water (0.05~oTFA) and ACN (48.0%; ACN up to 62.0%; in 8 min); Detector, UV 254nm.5 After purification 2-([ 4-[(1 S,4S,5R)-5-[[5-cyclopropyl-3-(2,6-dichlorophenyl)- L2-oxazol-4-yl]methoxy ]-2-azabicyclo[2.2.1 ]heptan-2-yl]phenyl]formamido )ethane-1-sulfonic acid I-166(79.4 mg, 33%) as a light yellow solid. 1H-NMR (300 MHz, CD30D): o 7.69 (d, J = 8.5 Hz,2H), 7.60---7.44 (m, 3H), 6.68 (d, J "' 8.4 Hz, 2H), 4.32 (s, 2H), 4.19 (s, lH), 3.80 (t, J '" 6.2Hz, 2H), 3.52 (d, J '" 6.1 Hz, lH), 3.42 (dd, J '" 9.8, 4.1 Hz, HI), 3.08 (t, J" 6.5 Hz, 2H), 2.7110 (d, J = 9.8 Hz, 1H), 2.53 (s, 1H), 2.26 (p, J = 6.9 Hz, 1H), 1.92- 1. 78 (m, lH), 164 (s, 2H),1.32 (d, J = 13.5 Hz, lH), 1.22-- 1.11 (m, 4H): MS (ES, mlz): [M+ l] = 606.2.

Reference： [1]Patent: WO2018/39386,2018,A1 .Location in patent: Page/Page column 322; 323

76
[ 3687-18-1 ]
[ 26113-25-7 ]
C₁₈H₃₄ClN₅O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35 mg	With N-ethyl-N,N-diisopropylamine; In water; at 20℃; for 4h;	(3-Aminopropane-1-sulfonic acid, 151 mg, 1.084 mmol, 2 eq) was dissolved completely in 5 ml of distilled water. Hunig base (472 ul, 2.71 mmol, 5 eq) To prepare a mixed solution. The compound 2-1 synthesized in Preparation Example 1(0.542 mmol, 1 eq) was added a mixed solution of 3-aminopropane-1-sulfonic acid The reaction proceeds at room temperature for 4 hours. After the reaction was completed, Obtained as a white solid and then subjected to silica gel chromatography to obtain pure compound 1-2(35 mg, 14.8%).

Reference： [1]Patent: KR101833020,2018,B1 .Location in patent: Paragraph 0086-0091

77
[ 3687-18-1 ]
[ 1645-65-4 ]
[ 2052-49-5 ]
C₁₁H₁₂F₃N₂O₃S₂^(1-)*C₁₆H₃₆N⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 7761 - 7773

78
[ 3687-18-1 ]
[ 2052-49-5 ]
[ 1548-13-6 ]
C₁₁H₁₂F₃N₂O₄S^(1-)*C₁₆H₃₆N⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 7761 - 7773

79
[ 3687-18-1 ]
[ 40846-94-4 ]
ADM_12 [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 1094 - 1098

80
[ 3687-18-1 ]
C₂₉H₄₄ClN₃O₇ [ No CAS ]
[ 68-12-2 ]
C₃₃H₅₀ClN₄O₁₁S^(1-)*Na⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%		The probe 4 (0.581 g, 1.0 mmol) and 4-dimethylaminopyridine (0.146 g, 1.2 mmol) were dissolved in 20 ml of anhydrous dimethylformamide.Under argon protection, a solution of phenyl p-nitrochloroformate (0.242 g, 1.2 mmol) in 10 ml of anhydrous dichloromethane was slowly added dropwise, and the mixture was stirred at room temperature for 1 h. After completion of the reaction, 3-amino-propanesulfonic acid was added. Add sodium (0.168 g, 1.2 mmol), add anhydrous triethylamine (0.16 ml, 1.2 mmol), and stir at room temperature for 30 min under Ar-protection conditions. After completion of the reaction, the solvent is evaporated to dryness and the residue is separated by reverse phase column to obtain a probe. 0.397 g, yield 50%.

Reference： [1]Patent: CN109574880,2019,A .Location in patent: Paragraph 0182-0186

81
[ 3687-18-1 ]
N-(3-((2-aminoethyl)sulfonamido)propyl)-3-chloro-2-methyl-N-(2-(3-(3-methylpyridin-4-yl)phenyl)propan-2-yl)benzenesulfonamide [ No CAS ]
[ 530-62-1 ]
3-(3-(2-(N-(3-((3-chloro-2-methyl-(2-(3-(3-methylpyridin-4-yl)phenyl)propan-2-yl)phenyl)sulfonamido)propyl)sulfamoyl)ethyl)ureido)propane-1-sulfonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To Compound 24 (80 mg, 0.16 mmol) in DCM (1 mL) was added CDI (32 mg, 0.2 mmol) and the reaction was stirred at room temperature for 45 minutes. After the solvent was removed in vacuo, half of the residue was dissolved in DMF (1 mL), followed by the addition of Intermediate 18C (24 mg, 0.1 mmol) and DIEA (0.02 mL, 0.12 mmol). The reaction mixture was stirred at room temperature overnight and partitioned between EtOAc and water. The organic layer was washed with water and brine, dried over Na2S04, and concentrated. The residue was purified by silica gel chromatography (0 - 5% MeOH/DCM) to afford Compound 28A (42 mg, 68%). LCMS (method A): m/z 770.6 (M+H)+.

Reference： [1]Patent: WO2018/5801,2018,A2 .Location in patent: Page/Page column 207; 208; 210

82
[ 3687-18-1 ]
C₂₅H₁₆N₄O₄S₆ [ No CAS ]
C₂₈H₂₃N₅O₆S₇ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 15752 - 15756
Angew. Chem.,2019,vol. 131,p. 15899 - 15903,5

83
[ 3687-18-1 ]
[ 24424-99-5 ]
[ 2052-49-5 ]
tetrabutylammonium 3-((tert-butoxycarbonyl)amino)propane-1-sulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	In water; acetone; at 20℃;	3-Amino-1-propanesulfonic acid (300 mg, 2.15 mmol) was dissolved in water (3 mL) followed by the addition of tetrabutylammonium hydroxide (0.2 M, 11 mL). A solution of Boc20 (759 mg, 2.15 mmol) in acetone (8 mL) was then added to dropwise. The reaction mixture was stirred at room temperature overnight. The acetone was removed in vacuo and the remaining aqueous mixture was extracted with dichloromethane and the combined organic layers were dried and concentrated under vacuum to obtain the product as an oil (912 mg, 88%). dH (400 MHz, CDCIs) 3.31 (m, 10H, CH2), 2.87 (t, 2H, CH2), 1.99 (m, 2H, CH2), 1.65 (m, 8H, CH2), 1.45 (m, 8H, CH2), 1.41 (s, 9H, CH3), 1.01 (t, 12H, CH3).

Reference： [1]Patent: WO2019/241850,2019,A1 .Location in patent: Paragraph 0242

84
[ 3687-18-1 ]
4‐(3‐bromo‐4‐fluorophenyl)‐3‐(4‐nitro‐1,2,5‐oxadiazol‐3‐yl)‐4,5‐dihydro‐1,2,4‐oxadiazol‐5‐one [ No CAS ]
sodium 3-((4-(4-(3-bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-1,2,5-oxadiazol-3-yl)amino)propane-1-sulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With sodium hydroxide; In water; N,N-dimethyl-formamide;	Toa mixture of amine or hydroxylamine derivatives (128 mmol) and NaOH (3.8 g,96mmol) in DMF (50 mL) and H2O (10 mL) was added 4-(3-bromo- 4-fluorophenyl)-3-(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,4-oxadiazol-5(4H)-one(12 g, 32 mmol) in DMF (30 mL). The reaction mixture was stirred at roomtemperature and the reaction progress was monitored by TLC. After fullconversion, the mixture was diluted with water and the solution was filtered togive product.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2020,vol. 30

85
[ 3687-18-1 ]
[ 1877-71-0 ]
C₁₂H₁₅NO₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	Stage #1: benzene 1,3-dicarboxylic acid monomethyl ester With triethylamine; HATU In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: Homotaurin In N,N-dimethyl-formamide at 20℃;	56 Monomethyl isophthalate 56a (500mg, 2.77mmol), 2-(7-azabenzotriazole)-N,N,N',N'-tetramethylurea hexafluorophosphate (HATU, 1023mg, 3.32mmol) and triethylamine (561mg, 5.54mmol) were sequentially added to N,N-dimethylformamide (6mL), stirred at room temperature and reacted for 1 hour, then 3-amino-1-propanesulfonic acid (579mg , 4.16mmol), continue to stir the reaction at room temperature.After the completion of the reaction was detected by TLC, ethyl acetate (20 mL) was added to dilute the reaction solution, the reaction solution was extracted with water (20 mL), and the aqueous phase was washed with ethyl acetate (20 mL).After the solvent was evaporated from the aqueous phase under reduced pressure, it was purified by silica gel column chromatography (dichloromethane: methanol = 15:1) to obtain compound 56b (white solid, 420 mg, yield 50%).

Reference： [1]Current Patent Assignee: CHINA PHARMACEUTICAL UNIVERSITY - CN111763201, 2020, A Location in patent: Paragraph 0355; 0359; 0361

86
[ 3687-18-1 ]
[ 2597010-57-4 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
97%	With sodium hydroxide In water at 50℃; for 3h;	14 Example 14 Sodium 3-((((2,2-dipentyl-1,3-dioxolan-4-yl)methoxy)carbonyl)amino)propane-1-sulfonate (JZ-0177) To a round bottom flask with (2,2-dipentyl-1,3-dioxolan-4-yl)methyl (4-nitrophenyl) carbonate (205 mg, 0.5 mmol), 3-aminopropane-1-sulfonic acid (104 mg, 0.75 mmol) and 5 mL can, 1M NaOH aq solution (1 mL) at RT was added. The reaction was stirred at 50°C for 3h. The crude mixture was then concentrated on vacuum, purified by flash column. A white color solid product was obtained (210 mg, 97%). 1H NMR (400 MHz, DMSO-d6): d 7.24 (t, J = 5.8 Hz, 1H), 4.19 (qd, J = 6.7, 4.2 Hz, 1H), 4.09 - 3.97 (m, 2H), 3.87 (dd, J = 11.4, 6.5 Hz, 1H), 3.57 (dd, J = 8.2, 6.9 Hz, 1H), 3.01 (q, J = 6.7 Hz, 2H), 2.43 - 2.35 (m, 2H), 1.68 (m, 2H), 1.52 (m, 4H), 1.36 - 1.15 (m, 12H), 0.90 - 0.80 (m, 6H). MS m/z 408 [M - Na - H]-.

Reference： [1]Current Patent Assignee: PROMEGA CORP - WO2021/26316, 2021, A1 Location in patent: Paragraph 0149

87
[ 156-87-6 ]
[ 3687-18-1 ]

Yield	Reaction Conditions	Operation in experiment
96.5%	Stage #1: propan-1-ol-3-amine With sulfur trioxide; sodium iodide at 110℃; for 0.75h; Inert atmosphere; Stage #2: With hydrogenchloride In water at 20℃;	1-7; 1 Add 20g of tetrabutyl titanate and 150mL of absolute ethanol into a round bottom flask and mix well, then add 100mL of deionized water and stir for 30min at room temperature, then heat to 80, stir for 30min, and then add 20wt% HNO3 dropwise. During the addition process, the solution will gradually become turbid. When the ratio of n(HNO3) to n(tetrabutyl titanate) is 4, stop adding nitric acid; after stirring for 3h, the colloidal solution will be generated according to the doping amount of molybdenum Add 2.8ml of ammonium molybdate solution containing 0.25g/mL of molybdenum, and continue to stir for 10h, and filter to obtain a stable molybdenum-doped nano-TiO2 sol. After washing and drying, it is calcined in a muffle furnace at 400 for 8h to obtain molybdenum-doped sol. Hybrid nano-titanium dioxide.Add 500g of 3-aminopropanol with a concentration of 25wt%, 12.5g of sodium iodide, and 30.0g of molybdenum-doped titanium dioxide into the reactor. The stirring speed of self-priming slurry is 800r/min. The temperature is increased to 110°C and diluted with nitrogen. 45% concentration of standard gas SO3, maintain the pressure at 8.0MPa, after 45 minutes of reaction, reduce to room temperature, discharge excess SO3; add 20wt% hydrochloric acid dropwise to the reaction kettle until the system pH=6; take 500g of mother liquor after pickling , Add 562.5g of ethanol and 187.5g of isopropanol to the mother liquor, adjust the speed to 100r/min and fully stir, set the cooling program of 1.0/min, the end of the cooling is -15, and after the crystal is cultivated for 60min, add the mother liquor to the centrifuge In the machine, centrifuge at 1500r/min, centrifuge for 10min, add 25g of anhydrous ethanol and methanol mixture at -15 to rinse, centrifuge again for 1min, and dry at 80 to obtain qualified 3-aminopropanesulfonic acid. The yield is 96.5%, and the purity is 99.8%.

Reference： [1]Current Patent Assignee: WANHUA CHEMICAL GROUP CO LTD - CN112724049, 2021, A Location in patent: Paragraph 0037-0059

88
[ 3687-18-1 ]
[ 77-09-8 ]
[ 2748657-91-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate In 1-methyl-pyrrolidin-2-one; water at 160 - 180℃; for 10h; Inert atmosphere; Autoclave;	1-7 Example 7 Add 4.0L of NMP/water (4:1) mixed solvent to a stainless steel autoclave equipped with a water trap, and then phenolphthalein (2mol, 636g) and 3-aminopropanesulfonic acid (2.04mol, 284g) are suspended in In the solvent, a weak base potassium carbonate (1.02 mol, 141 g) was added under stirring conditions. Subsequently, vacuum degassed three times, heated to 160°C under nitrogen protection, and reacted for 4 hours. After the water output stabilized, the water separator valve was closed. The temperature was increased to 180°C, while the pressure was adjusted to 1.0 MPa, and the reaction was continued for 6 hours. After cooling to room temperature, dichloromethane was added and filtered. Washed with dichloromethane several times to obtain a solid powder. The conversion rate tested by proton nuclear magnetic resonance spectrum was 87.0%. Finally, the solid powder obtained by filtration is recrystallized with ethanol to obtain the target product, and the separation yield reaches more than 80%.

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN113636969, 2021, A Location in patent: Paragraph 0037-0053

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 3687-18-1 ] {[proInfo.proName]}

Quality Control of [ 3687-18-1 ]

Related Doc. of [ 3687-18-1 ]

Product Details of [ 3687-18-1 ]

Calculated chemistry of [ 3687-18-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 3687-18-1 ]

Application In Synthesis of [ 3687-18-1 ]

[ 3687-18-1 ] Synthesis Path-Upstream 1~8

[ 3687-18-1 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 3687-18-1 ]

Aliphatic Chain Hydrocarbons

Sulfonic Acids

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 3687-18-1 ]