[ CAS No. 35665-38-4 ] {[proInfo.proName]}

Name: 35665-38-4|Fmoc-Gly-Gly-OH|98%
Brand: Ambeed
SKU: A432163
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2D 3D

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Quality Control of [ 35665-38-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 35665-38-4 ]

SDS Specification

Alternatived Products of [ 35665-38-4 ]

Product Details of [ 35665-38-4 ]

CAS No. :	35665-38-4	MDL No. :	MFCD00190880
Formula :	C₁₉H₁₈N₂O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FBKUOPULLUJMOC-UHFFFAOYSA-N
M.W :	354.36	Pubchem ID :	7019069
Synonyms :

Calculated chemistry of [ 35665-38-4 ]

Physicochemical Properties

Num. heavy atoms :	26
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.21
Num. rotatable bonds :	9
Num. H-bond acceptors :	5.0
Num. H-bond donors :	3.0
Molar Refractivity :	92.98
TPSA :	104.73 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.04 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.63
Log Po/w (XLOGP3) :	2.0
Log Po/w (WLOGP) :	1.73
Log Po/w (MLOGP) :	1.27
Log Po/w (SILICOS-IT) :	1.88
Consensus Log Po/w :	1.7

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-3.04
Solubility :	0.32 mg/ml ; 0.000903 mol/l
Class :	Soluble
Log S (Ali) :	-3.83
Solubility :	0.0529 mg/ml ; 0.000149 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.24
Solubility :	0.00203 mg/ml ; 0.00000571 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.45

Safety of [ 35665-38-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 35665-38-4 ]

* 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 [ 35665-38-4 ]
Downstream synthetic route of [ 35665-38-4 ]

[ 35665-38-4 ] Synthesis Path-Upstream 1~8

1
[ 556-50-3 ]
[ 28920-43-6 ]
[ 35665-38-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium carbonate In 1,4-dioxane; water at 20℃; for 12 h;	To the mixture of the two solids, the diglycine (1 mmol) and Fmoc chloride (1.2 mmol) was added 15 mL of dioxane and after cooling the same volume of 1N Na₂CO₃ solution was added and reaction mixture was stirred at RT for 12 h. After completion of reaction monitored by TLC the solution was acidified with HCl (1M) until pH 4-5 at 0°C and extracted with EtOAc (3 X 70 mL). The combined organic layers were dried (Na₂SO₄) and evaporated affording the pure N-Fmoc-GG-OH (2) (yield 89percent).

Reference： [1] Inorganica Chimica Acta, 2016, vol. 450, p. 211 - 215
[2] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 5, p. 1241 - 1247

2
[ 56-40-6 ]
[ 113484-74-5 ]
[ 35665-38-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydrogencarbonate In tetrahydrofuran; 1,2-dimethoxyethane; water for 20 h;	For Fmoc-GlyGly-OH 1a, Glycine (75 mg, 1 mmol) and NaHCO₃ (100 mg, 1.2 mmol) were dissolved in H₂O (10 ml) and dimethoxyethane (DME) (5 ml). Fmoc-Gly-NHS solution in DME (5 ml, 1 mmol) was added. THF (2.5 ml) was added, the mixture was sonicated to make it homogeneous and stirred for 20 h. All volatiles were removed on a rotovap, the residue was treated with EtOAc and 5percent KHCO₃ solution in H₂O. Product was extracted four times with EtOAc, washed with brine at pH=3, dried (Na₂SO₄), concentrated and dried in vacuo. Yield 321 mg (90percent). MS: 775.0 [2M +2Na]⁺; 377.4 [M+Na]⁺; 355.1 [M+1]⁺.

Reference： [1] Patent: WO2015/21092, 2015, A1, . Location in patent: Page/Page column 37
[2] Journal of the American Chemical Society, 2003, vol. 125, # 45, p. 13680 - 13681

3
[ 556-50-3 ]
[ 1131148-55-4 ]
[ 35665-38-4 ]

Reference： [1] Synlett, 2011, # 14, p. 2013 - 2016

4
[ 556-50-3 ]
[ 35665-38-4 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 10, p. 3103 - 3108

5
[ 29022-11-5 ]
[ 35665-38-4 ]

Reference： [1] European Journal of Organic Chemistry, 2010, # 17, p. 3275 - 3280
[2] Patent: WO2015/21092, 2015, A1,
[3] Organic Process Research and Development, 2017, vol. 21, # 10, p. 1533 - 1541

6
[ 35661-61-1 ]
[ 56-40-6 ]
[ 35665-38-4 ]

Reference： [1] Journal of Organic Chemistry, 1972, vol. 37, # 22, p. 3404 - 3409

7
[ 28920-43-6 ]
[ 35665-38-4 ]

Reference： [1] Synlett, 2011, # 14, p. 2013 - 2016
[2] Organic Process Research and Development, 2017, vol. 21, # 10, p. 1533 - 1541

8
[ 1370440-28-0 ]
[ 35665-38-4 ]

Reference： [1] Organic Process Research and Development, 2017, vol. 21, # 10, p. 1533 - 1541

[ 35665-38-4 ] Synthesis Path-Downstream 1~11

1
[ 556-50-3 ]
[ 28920-43-6 ]
[ 35665-38-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium carbonate In 1,4-dioxane; water at 20℃; for 12h;	Synthesisof intermediate 2 To the mixture of the two solids, the diglycine (1 mmol) and Fmoc chloride (1.2 mmol) was added 15 mL of dioxane and after cooling the same volume of 1N Na2CO3 solution was added and reaction mixture was stirred at RT for 12 h. After completion of reaction monitored by TLC the solution was acidified with HCl (1M) until pH 4-5 at 0°C and extracted with EtOAc (3 X 70 mL). The combined organic layers were dried (Na2SO4) and evaporated affording the pure N-Fmoc-GG-OH (2) (yield 89%).
77%	With sodium carbonate In 1,4-dioxane; water at 20℃;

Reference： [1]Gaisin, Zeev; Gellerman, Gary; Meyerstein, Dan [Inorganica Chimica Acta, 2016, vol. 450, p. 211 - 215]
[2]Kupihar, Zoltan; Schmel, Zoltan; Kele, Zoltan; Penke, Botond; Kovacs, Lajos [Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 5, p. 1241 - 1247]

2
[ 56-40-6 ]
[ 113484-74-5 ]
[ 35665-38-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydrogencarbonate; In tetrahydrofuran; 1,2-dimethoxyethane; water; for 20h;	For Fmoc-GlyGly-OH 1a, Glycine (75 mg, 1 mmol) and NaHCO3 (100 mg, 1.2 mmol) were dissolved in H2O (10 ml) and dimethoxyethane (DME) (5 ml). <strong>[113484-74-5]Fmoc-Gly-NHS</strong> solution in DME (5 ml, 1 mmol) was added. THF (2.5 ml) was added, the mixture was sonicated to make it homogeneous and stirred for 20 h. All volatiles were removed on a rotovap, the residue was treated with EtOAc and 5% KHCO3 solution in H2O. Product was extracted four times with EtOAc, washed with brine at pH=3, dried (Na2SO4), concentrated and dried in vacuo. Yield 321 mg (90%). MS: 775.0 [2M +2Na]+; 377.4 [M+Na]+; 355.1 [M+1]+.

Reference： [1]Patent: WO2015/21092,2015,A1 .Location in patent: Page/Page column 37
[2]Journal of the American Chemical Society,2003,vol. 125,p. 13680 - 13681

3
[ 35661-60-0 ]
[ 35665-38-4 ]
[ 1122069-12-8 ]
[ 161452-54-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: Fmoc-Leu-OH With diisopropyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere; solid phase reaction; Stage #2: With dmap In N,N-dimethyl-formamide at 20℃; for 2h; solid phase reaction; Stage #3: 2-[2-{({(9H-fluoren-9-yl)methoxy}carbonyl)amino}acetamido]acetic acid Further stages;

Reference： [1]Location in patent: experimental part Haddoub, Rose; Dauner, Martin; Stefanowicz, Fiona A.; Barattini, Valeria; Laurent, Nicolas; Flitsch, Sabine L. [Organic and Biomolecular Chemistry, 2009, vol. 7, # 4, p. 665 - 670]

4
[ 556-50-3 ]
[ 1131148-55-4 ]
[ 35665-38-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine In water; acetonitrile at 20℃; for 2h;

Reference： [1]Ibrahim, Tarek S.; Tala, Srinivasa R.; El-Feky, Said A.; Abdel-Samii, Zakaria K.; Katritzky, Alan R. [Synlett, 2011, # 14, p. 2013 - 2016]

5
[ 31972-52-8 ]
[ 35665-38-4 ]
[ 77128-70-2 ]
GGGGS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: N-(9-fluorenylmethoxycarbonyl)sarcosine In dichloromethane Inert atmosphere; Stage #2: With piperidine In methanol; dichloromethane; N,N-dimethyl-formamide for 0.35h; Inert atmosphere; Stage #3: Boc-Gly-Gly-OH; 2-[2-{({(9H-fluoren-9-yl)methoxy}carbonyl)amino}acetamido]acetic acid Further stages;	Synthesis of H-GGGGS-OH(5) Compound 5 was synthesized by solid phase from Boc-GG-OH, Fmoc-GG-OH and Fmoc-Sar-OH similarly as for product 1 accept coupling to deprotected sarcosine.Thus, 2-chlorotritylchloride resin (1.12 mmol/gr) was placed in a reactor and suspended in DCM under nitrogen atmosphere. Then a mixture of Fmoc-Sar-OH (2, 2 eq.) and DIPA (8eq.) in DCM was added. The resin loading reaction was allowed to proceed for4-5 hr and then the resin was capped by an addition of a few drops of methanol. The Fmoc protecting group was removed with 20% piperidine/DMF (3 x 7 min). Then, Fmoc-GG-OH (1.0 eq.) was dissolved in dichloroethane (0.20 M), triphosgene (0.4eq.) was added followed by careful addition of collidine (3 eq.) to the vigorously stirred mixture. After 2 mins, preactivated mixture was poured toreaction vessel and coupling was procced for 2h at rt. In the next step, Fmoc was removed by above mentioned procedure, and Boc-GG-OH (3 eq), was coupled to the peptidyl resin by PyBop (3 eq) as mentioned for 1. The cleavage and isolation as for 1 yielded finally the desired 5. Purification was conducted on semi-preparative HPLC (CH3CN/0.1% TFA in H2O) leading to pure product 5 at 84% yield.

Reference： [1]Gaisin, Zeev; Gellerman, Gary; Meyerstein, Dan [Inorganica Chimica Acta, 2016, vol. 450, p. 211 - 215]

6
[ 857478-30-9 ]
9-fluorenylmethoxycarbonyl Gly-Gly-Gly-OH [ No CAS ]
N-(tert-butyloxycarbonyl)-O-(tert-butyl)-N-methyl-L-tyrosine [ No CAS ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 35665-38-4 ]
[ 2035-75-8 ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 71989-23-6 ]
[ 71989-38-3 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 132327-80-1 ]
[ 94744-50-0 ]
[ 143824-78-6 ]
[ 204777-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
Me-Tyr-Aib-Glu-Gly-Thr-Iva-Ile-Ser-Asp-Tyr-Ser-Ile-Aib-Lys(Hda-GGGGG-)-Asp-Arg-Aib-Ala-Gln-Aib-Asn-Phe-Val-Asn-Trp-Iva-Leu-Ala-Gln-Arg-Pro-Ser-Ser-Gly-Ala-Pro-Pro-Pro-Ser-NH₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.9 mg		Sieber amide resin (0.71 meq/g, 352 mg, 0.25 mmol) was added to a reaction tube, which was then set in a peptide synthesizer, and amino acids were sequentially extended according to the protocol using 20% piperidine/NMP [reacted at room temperature for 15 minutesj to deprotect the Fmoc group and 5 equivalents of Fmoc-amino acids/DIPCDJIOxyma [reacted at room temperature for 150 minutesj to condense the Fmoc-amino acids.The operation wherein the obtained BocMe-Tyr(tBu)-Aib-Glu(OtB u)-Gly-Thr(tBu)-Iva-Ile-Ser(tBu)-Asp(OtB u)-Tyr(tB u)-Ser( tB u)-Ile-Aib-Lys(ivDde)-Asp(OtBu)-Arg(Pbf)-Aib-Ala-Gln(Trt)-Aib-Asn(Trt)-Phe-Va l-Asn(Trt)-Trp(Boc)-Iva-Leu-Ala-Gln(Trt)-Arg(Pbf)-Pro-Ser(tBu)-Ser(tB u)-Gly-Ala-Pro-Pro-Pro-Ser(tBu)-Sieber amide resin was suspended in a 2% hydrazine/NMP solution, the resulting suspension was stirred at room temperature for 3 hours, and then the solution was removed by filtration was repeated twice to deprotect the ivDde group of Lys at position 14.Subsequently, the resin was washed with MeOH, and dried under reduced pressure to thereby obtain 1.87 g of BocMe-Tyr(tBu)-Aib-Glu(OtB u)-Gly-Thr(tBu)-Iva-Ile-Ser(tBu)-Asp(OtB u)-Tyr(tB u)-Ser( tB u)-Ile-Aib-Lys-Asp(OtBu)-Arg(Pbf)-Aib-Ala-Gln(Trt)-Aib-Asn(Trt)-Phe-Val-Asn( Trt)-Trp(Boc)-Iva-Leu-Ala-Gln(Trt)-Arg(Pbf)-Pro-Ser(tB u)-Ser(tBu)-Gly-Ala-Pro-Pro-Pro-Ser(tBu)-Sieber amide resin.37.3 mg (0.005 mmol) of the obtained resin was weighed into a reaction tube, which was then set in a peptide synthesizer. Subsequently, Fmoc-Gly-Gly-OH and FmocGly-Gly-Gly-OH was introduced using the peptide synthesizer, according to the protcol using 20% piperidine/NMP [reacted at 50C for 5 minutesj to deprotect the Fmoc group and 5 equivalents of Fmoc-amino acids/DIPCDJIOxyma [50C, 15 minutesj to condense the Fmoc-amino acids, and then BocMe-Tyr(tBu)-Aib-Glu(OtB u)-Gly-Thr(tBu)-Iva-Ile-Ser(tBu)-Asp(OtB u)-Tyr(tB u)-Ser( tB u)-Ile-Aib-Lys(H-Gly-Gly-Gly-Gly-Gly-)-Asp(OtBu)-Arg(Pbf)-Aib-Ala-Gln(Trt)-A ib-Asn(Trt)-Phe-Val-Asn(Trt)-Trp(Boc)-Iva-Leu-Ala-Gln(Trt)-Arg(Pbf)-Pro-Ser(tB u)Ser(tBu)-Gly-Ala-Pro-Pro-Pro-Ser(tBu)-Sieber amide resin was obtained. In this case, the condensation reaction was carried out using the double coupling method in which after all the reactions at 50C for 15 minutes, the solution was removed by filtration, and the same condensation reaction was repeated. To the obtained resine, 6.4 mg of adipic anhydride, 6.4 mg of DIPEA, and NMP (0.1 ml) were added, and then the solution was stirred at room temperature for 2 hours. After removal of the reaction solution by filtration, the resin was washed with MeOH, and dried under reduced pressure to thereby obtain 36.9 mg of the protected peptide resin of interest, BocMe-Tyr(tBu)-Aib-Glu(OtB u)-Gly-Thr(tBu)-Iva-Ile-Ser(tBu)-Asp(OtB u)-Tyr(tB u)-Ser( tB u)-Ile-Aib-Lys(Hda-GGGGG-)-Asp(tBu)-Arg(Pbf)-Aib-Ala-Gln(Trt)-Aib-Asn(Trt)Phe-Val-Asn(Trt)-Trp(Boc)-Iva-Leu-Ala-Gln(Trt)-Arg(Pbf)-Pro-Ser(tBu)-Ser(tBu)-Gl y-Ala-Pro-Pro-Pro-Ser(tB u)-Sieber amide resin.Subsequently, to the total amount of the obtained resin, 0.5 mL of TFA:m-cresol:thioanisole:ethandithiol:H20:triisopropylsilane (80:5:5:5:2.5:2.5) was added and the resulting mixture was stirred for 1.5 hours. Diethyl ether was added to the reaction solution to obtain a precipitate and after centrifugation the supernatant was removed. This operation was repeated twice and the precipitate was washed. The residue was extracted with a 90% acetic acid aqueous solution and the resin was removed by filtration, and then the purification was carried out by preparative HPLCusing Phenomenex Kinetex 5iim XB-C18 (250x20.0 mm I.D.) by the linear concentration gradient elution (60 minutes) with solution A: 0.1% TFA-water and solution B: 0.1% TFA-containing acetonitrile at a flow rate of 8 mL/minute from A/B: 66/34 to 56/44, and fractions containing the product of interest were collected and freeze-dried to thereby obtain 2.9 mg of a white powder.Mass spectrometry result: (M+H)+ 46 16.573 (calculated 4616.32) HPLC elution time: 4.09 minutesElution conditions:Column: Kinetex 1.7 lIm C8 bOA, (100 x 2.1 mm I.D.)Eluents: Using solution A: 0.1% TFA-water, solution B: 0.1% TFA-containing acetonitrile, A/B: 80/20 to 30/70. Linear concentration gradient elution (10 minutes). Flow rate: 0.5 mL/minutesTemperature: 40C

Reference： [1]Patent: WO2018/181864,2018,A1 .Location in patent: Paragraph 0554

7
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 35665-38-4 ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-18-9 ]
[ 71989-23-6 ]
[ 132388-68-2 ]
[ 111061-56-4 ]
[ 111061-54-2 ]
[ 129223-22-9 ]
[ 143824-78-6 ]
C₈₅H₁₂₆N₂₂O₂₄ [ No CAS ]

Reference： [1]Green Chemistry,2019,vol. 21,p. 6451 - 6467

8
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 35665-38-4 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 109425-51-6 ]
[ 104091-08-9 ]
[ 109745-15-5 ]
[ 143824-78-6 ]
[ 148928-15-8 ]
C₁₀₆H₁₅₀N₂₆O₃₈S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: Fmoc-Thr(tBu)-OH With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; Inert atmosphere; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; 2-[2-{({(9H-fluoren-9-yl)methoxy}carbonyl)amino}acetamido]acetic acid; Fmoc-(tBu)Asp-OH; Fmoc-Glu(OtBu)-OH; N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine; Fmoc-His(Trt)-OH; Fmoc-Glu(OtBu)-OH; (R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; 1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-4-carboxylic acid Further stages;	14 [00562] Exemplary Peptide Synthesis. Peptide were synthesized using standard Fmoc chemistry, for example: (1429) 1) Add DCM to the vessel containing CTC Resin (1.00 mmol, 1.00 g, 1.00 mmol/g) and Fmoc- Thr(tBu)-OH (3218 mg, 0.800 mmol, 0.80 eq ) with N2 bubbling. (1430) 2) Add DIE A (4.00 eq) dropwise and mix for 2 hours. (1431) 3) Add MeOH (1.00 mL) and mix for 30 min. (1432) 4) Drain and wash with DMF for 5 times. (1433) 5) Add 20% piperidine/DMF and react on 30 min. (1434) 6) Drain and wash with DMF for 5 times. (1435) 7) Add Fmoc-amino acid solution and mix for 30 sec first, then add activation solution, and the coupling reaction lasts for 1 hr with continuous N2 bubbling. (1436) 8) Repeat step 4 to 7 for next amino acid coupling. (1437) (1438) Synthesis scale: 0.8 mmol (1439) 20% piperidine in DMF was used for Fmoc deprotection for 30 min. (1440) The coupling reaction was monitored by ninhydrin test. (1441) After last amino acid coupling, N-terminal Fmoc was removed, and the resin was washed with MeOH for 3 times, and then dried under vacuum. (1442) Peptide Cleavage and Purification: (1443) Add cleavage cocktail (95%TFA/2.5%EDT/2.5%H20/2.5%TIS) to the flask containing the side chain protected peptide at room temperature and stir for 2 hr. (1444) The peptide is precipitated with cold isopropyl ether and collected by centrifugation (3 min at 3000 rpm). (1445) The precipitate is washed with cold isopropyl ether for two additional times. (1446) Dry the crude peptide under vacuum for 2 hr. (1447) Dissolve the crude peptide in ACN/FhO (1 : 1, 800 mL in total) (1448) Adjust pH to 8 by NaHCCb and stir for 16 hr, and the disulfide bond is formed through air oxidation, where the completion of the reaction is indicated by LCMS. (1449) Lyophilize the reaction mixture to get the crude peptide. (1450) Purify the crude peptide by prep-HPLC (TFA condition) to give the compound 2 (102 mg).
	Stage #1: Fmoc-Thr(tBu)-OH With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; Inert atmosphere; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.5h; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; 2-[2-{({(9H-fluoren-9-yl)methoxy}carbonyl)amino}acetamido]acetic acid; Fmoc-(tBu)Asp-OH; Fmoc-Glu(OtBu)-OH; N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine; Fmoc-His(Trt)-OH; Fmoc-Glu(OtBu)-OH; (R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; 1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-4-carboxylic acid Further stages;	1 Exemplary Peptide Synthesis. Peptide were synthesized using standard Fmoc chemistry, for example: 1) Add DCM to the vessel containing CTC Resin (1.00 mmol, 1.00 g, 1.00 mmol/g) and Fmoc- Thr(tBu)-OH (3218 mg, 0.800 mmol, 0.80 eq) with N2 bubbling. 2) Add DIEA (4.00 eq) dropwise and mix for 2 hours. 3) Add MeOH (1.00 mL) and mix for 30 min. 4) Drain and wash with DMF for 5 times. 5) Add 20% piperidine/DMF and react on 30 min. 6) Drain and wash with DMF for 5 times. 7) Add Fmoc-amino acid solution and mix for 30 sec first, then add activation solution, and the coupling reaction lasts for 1 hr with continuous N2 bubbling. 8) Repeat step 4 to 7 for next amino acid coupling. Synthesis scale: 0.8 mmol 20% piperidine in DMF was used for Fmoc deprotection for 30 min. The coupling reaction was monitored by ninhydrin test. After last amino acid coupling, N-terminal Fmoc was removed, and the resin was washed with MeOH for 3 times, and then dried under vacuum. Peptide Cleavage and Purification: Add cleavage cocktail (95%TFA/2.5%EDT/2.5%H2O/2.5%TIS) to the flask containing the side chain protected peptide at room temperature and stir for 2 hr. The peptide is precipitated with cold isopropyl ether and collected by centrifugation (3 min at 3000 rpm). The precipitate is washed with cold isopropyl ether for two additional times. Dry the crude peptide under vacuum for 2 hr. Dissolve the crude peptide in ACN/H2O (1:1, 800 mL in total) Adjust pH to 8 by NaHCO3 and stir for 16 hr, and the disulfide bond is formed through air oxidation, where the completion of the reaction is indicated by LCMS. Lyophilize the reaction mixture to get the crude peptide. Purify the crude peptide by prep-HPLC (TFA condition) to give the compound 2 (102 mg).

Reference： [1]Current Patent Assignee: BIOHAVEN PHARMACEUTICAL HOLDING COMPANY LTD - WO2020/132588, 2020, A1 Location in patent: Paragraph 00561; 00562
[2]Current Patent Assignee: KLEO PHARMACEUTICALS - WO2021/3050, 2021, A2 Location in patent: Paragraph 00649; 00650

9
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 35665-38-4 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 86060-81-3 ]
[ 109425-51-6 ]
[ 104091-08-9 ]
[ 88574-06-5 ]
[ 109745-15-5 ]
[ 143824-78-6 ]
[ 148928-15-8 ]
C₁₂₄H₁₈₂N₃₂O₄₂S₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine for 1h; Inert atmosphere; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.5h; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; 2-[2-{({(9H-fluoren-9-yl)methoxy}carbonyl)amino}acetamido]acetic acid; Fmoc-(tBu)Asp-OH; Fmoc-Glu(OtBu)-OH; N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine; Fmoc-Thr(tBu)-OH; S-[(acetylamino)methyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-cysteine; Fmoc-His(Trt)-OH; Fmoc-Glu(OtBu)-OH; 6-[(9H-fluoren-9-ylmethoxy)carbonyl]amino}hexanoic acid; (R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; 1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-4-carboxylic acid Further stages;	1 Exemplary Peptide Synthesis. Peptide were synthesized using standard Fmoc chemistry, for example: 1) Add DMF to the vessel containing Rink amide MBHA Resin (1.00 mmol, 2.27 g, sub: 0.440 mmol/g) and swell for 2 hours. 2) Drain and wash with DMF for 3 times. 3) Add 20% piperidine/DMF and mix for 30 min. 4) Drain and wash with DMF for 3 times. 5) Add Fmoc-amino acid solution and mix for 30 sec, then add coupling regents, and the coupling reaction lasts for 1 hr with continuous N2 bubbling. 6) Repeat step 2 to 5 for next amino acid coupling. Synthesis scale: 1.0 mmol 20% piperidine in DMF was used for Fmoc deprotection for 30 min. The coupling reaction was monitored by ninhydrin test. After last amino acid coupling, N-terminal Fmoc was removed, and the resin was washed with MeOH for 3 times, and then dried under vacuum. Peptide Cleavage and Purification: Add cleavage cocktail (95%TFA/2.5%EDT/2.5%H2O/2.5%TIS) to the flask containing the side chain protected peptide at room temperature and stir for 2 hr. The peptide is precipitated with cold isopropyl ether and collected by centrifugation (3 min at 3000 rpm). The precipitate is washed with cold isopropyl ether for two additional times. Dry the crude peptide under vacuum for 2 hr. Dissolve the crude peptide in ACN/H2O (1:1, 600 mL in total) Adjust pH to 8 by NaHCO3 and stir for 16 hr, and the first disulfide bond is formed through air oxidation, where the completion of the reaction is indicated by LCMS. Lyophilize the reaction mixture to get the crude peptide. Purify the crude peptide by prep-HPLC (A: 0.075 % TFA in H2O, B: ACN) to give the compound 2 (218 mg, 7.46% yield).

Reference： [1]Current Patent Assignee: KLEO PHARMACEUTICALS - WO2021/3050, 2021, A2 Location in patent: Paragraph 00639; 00640

10
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 35665-38-4 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 86060-81-3 ]
[ 109425-51-6 ]
[ 104091-08-9 ]
[ 109745-15-5 ]
[ 143824-78-6 ]
[ 148928-15-8 ]
C₁₁₈H₁₇₁N₃₁O₄₁S₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine for 1h; Inert atmosphere; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.5h; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; 2-[2-{({(9H-fluoren-9-yl)methoxy}carbonyl)amino}acetamido]acetic acid; Fmoc-(tBu)Asp-OH; Fmoc-Glu(OtBu)-OH; N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine; Fmoc-Thr(tBu)-OH; S-[(acetylamino)methyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-cysteine; Fmoc-His(Trt)-OH; Fmoc-Glu(OtBu)-OH; (R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; 1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-4-carboxylic acid Further stages;	1 Exemplary Peptide Synthesis. Peptide were synthesized using standard Fmoc chemistry, for example: 1) Add DMF to the vessel containing Rink amide MBHA Resin (1.00 mmol, 2.27 g, sub: 0.440 mmol/g) and swell for 2 hours. 2) Drain and wash with DMF for 3 times. 3) Add 20% piperidine/DMF and mix for 30 min. 4) Drain and wash with DMF for 3 times. 5) Add Fmoc-amino acid solution and mix for 30 sec, then add coupling regents, and the coupling reaction lasts for 1 hr with continuous N2 bubbling. 6) Repeat step 2 to 5 for next amino acid coupling. Synthesis scale: 1.0 mmol. 20% piperidine in DMF was used for Fmoc deprotection for 30 min. The coupling reaction was monitored by ninhydrin test. After last amino acid coupling, N-terminal Fmoc was removed, and the resin was washed with MeOH for 3 times, and then dried under vacuum. Peptide Cleavage and Purification: Add cleavage cocktail (95%TFA/2.5%EDT/2.5%H2O/2.5%TIS) to the flask containing the side chain protected peptide at room temperature and stir for 2 hr. The peptide is precipitated with cold isopropyl ether and collected by centrifugation (3 min at 3000 rpm). The precipitate is washed with cold isopropyl ether for two additional times. Dry the crude peptide under vacuum for 2 hr. Dissolve the crude peptide in ACN/H2O (1:1, 600 mL in total) Adjust pH to 8 by NaHCO3 and stir for 16 hr, and the first disulfide bond is formed through air oxidation, where the completion of the reaction is indicated by LCMS. Lyophilize the reaction mixture to get the crude peptide. Purify the crude peptide by prep-HPLC (A: 0.075 % TFA in H2O, B: ACN) to give compound 2 (248 mg, 8.84% yield).

Reference： [1]Current Patent Assignee: KLEO PHARMACEUTICALS - WO2021/3050, 2021, A2 Location in patent: Paragraph 00644; 00645

11
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 35665-38-4 ]
tert-butyl 12-aminododecanoate [ No CAS ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 109425-51-6 ]
[ 109745-15-5 ]
[ 143824-78-6 ]
[ 148928-15-8 ]
[ 204251-33-2 ]
C₁₁₈H₁₇₃N₂₇O₃₉S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: Fmoc-Thr(tBu)-OH With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; Inert atmosphere; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.5h; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; 2-[2-{({(9H-fluoren-9-yl)methoxy}carbonyl)amino}acetamido]acetic acid; tert-butyl 12-aminododecanoate; Fmoc-(tBu)Asp-OH; Fmoc-Glu(OtBu)-OH; N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine; Fmoc-His(Trt)-OH; (R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; 1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-4-carboxylic acid; γ-allyl (2R)-N-(fluoren-9-ylmethoxycarbonyl)glutamate Further stages;	1 Exemplary Peptide Synthesis. Peptide were synthesized using standard Fmoc chemistry, for example: 1) Add DCM to the vessel containing CTC Resin (0.500 mmol, 500 mg, 1.00 mmol/g) and Fmoc- Thr(tBu)-OH (159 mg, 0.400 mmol, 0.80 eq) with N2 bubbling. 2) Add DIEA (4.00 eq) dropwise and mix for 2 hours. 3) Add MeOH (0.50 mL) and mix for 30 min. 4) Drain and wash with DMF for 5 times. 5) Add 20% piperidine/DMF and react on 30 min. 6) Drain and wash with DMF for 5 times. 7) Add Fmoc-amino acid solution and mix for 30 sec first, then add activation solution, and the coupling reaction lasts for 1 hr with continuous N2 bubbling. 8) Repeat step 4 to 7 for next amino acid coupling. Synthesis scale: 0.4 mmol 20% piperidine in DMF was used for Fmoc deprotection for 30 min. Pd(PPh3)4 and phenylsilane was used for removing Ally group on the sidechain of D-Glu. The coupling reaction was monitored by ninhydrin test. After last amino acid coupling, N-terminal Fmoc was removed, and the resin was washed with MeOH for 3 times, and then dried under vacuum. Peptide Cleavage and Purification: Add cleavage cocktail (95%TFA/2.5%EDT/2.5%H2O/2.5%TIS) to the flask containing the side chain protected peptide at room temperature and stir for 2 hr. The peptide is precipitated with cold isopropyl ether and collected by centrifugation (3 min at 3000 rpm). The precipitate is washed with cold isopropyl ether for two additional times. Dry the crude peptide under vacuum for 2 hr. Dissolve the crude peptide in ACN/H2O (1:1, 600 mL in total) Adjust pH to 8 by NaHCO3 and stir for 16 hr, and the first disulfide bond is formed through air oxidation, where the completion of the reaction is indicated by LCMS. Lyophilize the reaction mixture to get the crude peptide. Purify the crude peptide by prep-HPLC (A: 0.075 % TFA in H2O, B: ACN) to give the compound 2 (42.0 mg).

Reference： [1]Current Patent Assignee: KLEO PHARMACEUTICALS - WO2021/3050, 2021, A2 Location in patent: Paragraph 00611; 00612

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P370 + P376	In case of fire: Stop leak if safe to Do so.
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Code	Phrase
H400	Very toxic to aquatic life
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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. 35665-38-4 ] {[proInfo.proName]}

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[ 35665-38-4 ] Synthesis Path-Upstream 1~8

[ 35665-38-4 ] Synthesis Path-Downstream 1~11

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