[ CAS No. 195202-08-5 ] {[proInfo.proName]}

Name: 195202-08-5|(S)-2-(3,4,5-Trimethoxyphenyl)butanoic acid|97%
Brand: Ambeed
SKU: A151284
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Quality Control of [ 195202-08-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 195202-08-5 ]

SDS Specification

Alternatived Products of [ 195202-08-5 ]

Product Details of [ 195202-08-5 ]

CAS No. :	195202-08-5	MDL No. :	MFCD06245370
Formula :	C₁₃H₁₈O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WBULUDGUWZFLMO-VIFPVBQESA-N
M.W :	254.28	Pubchem ID :	2771669
Synonyms :

Calculated chemistry of [ 195202-08-5 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.46
Num. rotatable bonds :	6
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	67.08
TPSA :	64.99 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.27 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.26
Log Po/w (XLOGP3) :	2.23
Log Po/w (WLOGP) :	2.29
Log Po/w (MLOGP) :	1.37
Log Po/w (SILICOS-IT) :	2.27
Consensus Log Po/w :	2.08

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.67
Solubility :	0.541 mg/ml ; 0.00213 mol/l
Class :	Soluble
Log S (Ali) :	-3.23
Solubility :	0.15 mg/ml ; 0.000589 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.0
Solubility :	0.254 mg/ml ; 0.001 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.58

Safety of [ 195202-08-5 ]

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 [ 195202-08-5 ]

* 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 [ 195202-08-5 ]
Downstream synthetic route of [ 195202-08-5 ]

[ 195202-08-5 ] Synthesis Path-Upstream 1~5

1
[ 195202-06-3 ]
[ 195202-08-5 ]

Yield	Reaction Conditions	Operation in experiment
21%	Stage #1: With cinchonidine In acetonitrileSeparation of racemate Stage #2: With hydrogenchloride In dichloromethane; waterSeparation of racemate	(lg) Step 7. Synthesis of (S)-2-(3,4,5-Trimethoxyphenyl)butyric acid (AP17360). AP14900 AP17360[195202-08-5]AP14900 (₅00 g, 1.97 moles) and (-)-cinchonidine (580 g, 1.97 moles) were charged into a 10 L reactor equipped with mechanical agitation. Acetonitrile (7500 mL) was added and the mixture heated to reflux for 30 minutes. The homogeneous solution was allowed to cool to room temperature with concomitant formation of salts. The solids were then filtered and the crystallization procedure was carried out an additional five times utilizing acetonitrile (7000, 7000, 6500, 6500, and 5000 mL) as solvent. The diastereomeric salt was then suspended in water (1400 mL) and dichloromethane (600 mL) and the solution was agitated until all salt was dissolved. The agitated mixture was adjusted to pH 2 by the addition of concentrated HCl, the organic layer was separated and the aqueous layer extracted with a further amount of CH₂C1₂ (2 300 mL). The combined organic layers were then washed with a 1 N HCl solution (2 200 mL) to remove any remaining (-)-cinchonidine. These acid washings were then reextracted with CH₂C1₂ (100 mL) and all CH₂C1₂ solutions were combined. The combined organic solutions were washed with a 10percent aqueous NaHC03 solution (200 mL), dried over anhydrous MgS04, concentrated on a rotary evaporator to a volume of -250 mL, and then hexane was added (500 mL). The solution was heated and cooled and an additional portion of hexane (200 mL) was added. The solution was then concentrated on a rotary evaporator until solids appeared and was allowed to sit overnight. The resultant solids were filtered, triturated with hexane (2 300 mL), and placed in a vacuum oven at 50 'C for 84 hours to afford product (105.0 g, 21percent) as an off-white solid: [a]²²_D +54.8 (c = 1.07, MeOH, 30 min, 99.1percent ee material); NMR (DMSO-d₆, 300 MHz) 6.34 (s, 2 H), 3.52 (s, 6 H), 3.40 (s, 3 H), 3.11 (t, J = 7.6 Hz, 1 H) 1.76-1.64 (m, 1 H), 1.46-1.36 (m, 1 H), 0.60 (t, J = 7.3 Hz, 3 H); ^l3C NMR (DMSO- d₆, 75 MHz) 175.1, 153.1, 136.9, 135.8, 105.4, 60.3, 56.2, 53.1, 26.7, 12.4. Anal. Calcd for C,₃H₁₈05: C, 61.41 ; H, 7.13. Found: C, 61.47; H, 7.20.

Reference： [1] Patent: WO2012/103279, 2012, A2, . Location in patent: Page/Page column 11-12

2
[ 1392284-67-1 ]
[ 195202-08-5 ]

Reference： [1] Patent: WO2012/103279, 2012, A2, . Location in patent: Page/Page column 15

3
[ 951-82-6 ]
[ 75-03-6 ]
[ 195202-08-5 ]

Reference： [1] Journal of Organic Chemistry, 2018, vol. 83, # 11, p. 6050 - 6055

4
[ 951-82-6 ]
[ 195202-08-5 ]

Reference： [1] Patent: WO2012/103279, 2012, A2,

5
[ 247118-51-0 ]
[ 195202-08-5 ]

Reference： [1] Patent: WO2012/103279, 2012, A2,

[ 195202-08-5 ] Synthesis Path-Downstream 1~14

Yield	Reaction Conditions	Operation in experiment
91%		(S)-2-(3,4,5-Trimethoxyphenyl)butyric acid (4S): A solution of 4 (3.09 g, 12.15 mmol) in CH3CN (130 mL) was treated with (-)-cinchonidine (3.58 g, 12.15 mmol) and the mixture heated to reflux. The homogeneous solution was allowed to slowly cool to room temperature with concomitant formation of salts. After a period of 1 h at room temperature, the solution was cooled to 0 C. for 30 minutes and the solution then filtered to afford 4.05 g of a chalky colorless solid. This recrystalliztion procedure was then carried out an addition four times utilizing ~20 mL CH3CN/g of salt. The diastereomeric salt isolated from the fifth crystallization (1.64 g) was suspended in EtOAc (100 mL) and treated with a 10% aqueous HCl solution (10 mL). The organic phase was then washed with water (2*15 mL) followed by brine 10 mL), dried over anhydrous MgSO4, and concentrated to afford product (0.75 g, 24%) as a colorless solid (91% ee by Chiralcel OD HPLC, 1:5:94 formic acid/i-PrOH/hexane, retention time 19.6 min for the R-enantiomer, and 22.1 min for the desired S-enantiomer): mp 84-85 C. (99.1% ee material); [a]22D +54.8 (c=1.07, MeOH, 30 min, 99.1% ee material); UV (MeOH) lmax 270 (e 895), 232 (e 7,440), 207 (e 40,994) nm; 1H NMR (DMSO-d6, 300 MHz) 6.34 (s, 2 H), 3.52 (s, 6 H), 3.40 (s, 3 H), 3.11 (t, J=7.6 Hz, 1 H) 1.76-1.36 (m, 1 H), 0.60 (t, J=7.3 Hz, 3 H); 1H NMR (CD30D, 300 MHz) 6.78 (s, 2 H), 4.00 (s, 6 H), 3.90 (s, 3 H), 3.55 (t, J=7.7 Hz, 1 H) 2.24-2.12 (m, 1 H), 1.97-1.83 (m, 1 H), 1.07 (t, J=7.3 Hz, 3 H); 13C NMR (DMSO-d6, 75 MHz) 175.1, 153.1, 136.9, 135.8, 105.4, 60.3, 56.2, 53.1, 26.7, 12.4; 13C NMR (CD3OD, 75 MHz) 178.1, 154.9, 138.7, 137.4, 106.8, 61.5, 57.0, 55.3, 28.3, 12.9; HRMS (FAB): (M-H)- calcd: 253.1076, meas: 253.1063. Anal. Calcd for C13H18O5: C, 61.41; H, 7.13. Found: C, 61.47; H, 7.20.
77%		2S-(3,4,5-Trimethoxyphenyl)butyric acid A solution of (4R-benzyl-2-oxazolidinonyl) 2S-(3,4,5-Trimethoxyphenyl)butyrimide (12.6 g, 30.6 mmol) in THF (75 mL) at 0 C. was slowly added to a slurry containing LiOH monohydrate (12.84,306 mmol) and hydrogen peroxide (34.7 mL of a 30% aqueous solution, 306 mmol) in a THF/water (2:1) solution at 0 C. The reaction mixture was allowed to stir for 30 min after which time EtOAC (1 L) was added and the solution slowly acidified to a pH of 3 with a 1N aqueous solution of HCl. The organic phase was washed with water (500 mL) followed by a saturated aqueous NaCl solution (250 mL), then dried over MgSO4, filtered, evaporated, and chromatographed (silica gel, 2.5% HOAc/48.75% EtOAc/48.75% hexanes) to afford product (5.99 g, 77%).

2
[ 195202-08-5 ]
[ 18650-39-0 ]
[ 195202-09-6 ]

Yield	Reaction Conditions	Operation in experiment
84%		Cpd9' (99 g, 0.39 mol) was dissolved in 1 L of dichloromethane, and (S)-piperidine-2-carboxylic acid methyl ester hydrochloride (71.3 g, 0.40 mol), 2-chloro-1-methylpyridine Iodide (CMPI, 126.4 g, 0.50 mol), triethylamine (165 ml, 1.167 mol) was added dropwise, and the reaction was completed at room temperature for 2 h. TLC showed the reaction was completed and concentrated directly to give an oil. 50 ml of water, and then added LiOH (81.8 g, 3.41 mol), stirred at room temperature overnight, TLC showed the reaction was complete;Post-reaction treatment: 500 ml of water was added dropwise to the reaction, 40 C, concentrated to remove methanol, then added EA 500 ml and water 200 ml, and the extract was separated, and the organic phase was saturated NaHCO.3After washing, water was added and the aqueous phase was separated. The combined aqueous phases were acidified to pH 4 with 2N HCl solution and filtered to give white solid Cpd6' (120 g, yield 84%).
73%		(lh) Step 8. Synthesis of [S-(R,R)]-l-[l-oxo-2-(3,4,5-trimethoxyphenyl)butyl]-2- piperdinecarboxylic acid (API 7362). A solution of AP17360 (10.0 g, 0.039 moles) in CH2C12 (100 mL) was treated with methyl-L- pipecolate hydrochloride (7.2 g, 0.04 moles) followed by 2-chloro-l-methylpyridinium iodide (12.77 g, 0.050 moles). The reaction mixture was then treated dropwise with triethylamine (16.66 mL, 0.120 moles) resulting in a 22C rise in the temperature of the reaction mixture. The solution was allowed to stir for 2 hours, after which time the CH2C12 was removed on a rotary evaporator, the residue (~ 50 mL volume) was dissolved in MeOH (60 mL), and the solution was treated with water (5 mL) followed by lithium hydroxide monohydrate (8.26 g, 0.197 moles). The mixture was stirred overnight then treated with water (20 mL) and the MeOH removed on a rotary evaporator at 40C. The resulting aqueous solution was treated with EtOAc (60 mL) followed by a saturated aqueous NaHC03 solution (60 mL) and the organic layer washed with water (10 mL). The combined aqueous layers were then acidified to pH 4 by careful addition of a 2N HC1 solution and the resulting suspension cooled to 10 C. The precipitate was filtered, triturated with a 1% aqueous citric acid solution (100 mL) and air dried under vacuum at 58 C to provide product, AP17362, (10.5 g, 73%): mp 173.5-174 "C; [ ] 2D +10.9 (c = 1.01, DMSO, 30 min); UV (MeOH) max 270 (epsilon 990), 232 (epsilon 11,161), 207 (epsilon 49,079) nm; NMR (DMSO- d6, 300 MHz) 6.55 (s, 2 H), 5.13 (d, J = 4.4 Hz, 1 H), 3.85-3.64 (m, 1 1 H), 2.77-2.70 (m, 1 H), 2.12 (d, J = 13.4 Hz, 1 H), 1.99-1.85 (m, 1 H), 1.65-1.55 (m, 4 H), 1.38-1.18 (m, 2 H), 0.84 (t, J = 7.2 Hz, 3 H); NMR (CD3OD, 300 MHz) 6.74 (s, 2 H), 5.43 (d, J = 4.0 Hz, 1 H), 4.13-3.83 (m, 1 1 H), 3.03 (td, J = 13.5, 3.0 Hz, 1 H), 2.44 (d, J = 13.8 Hz, 1 H), 2.24-2.14 (m, 1 H), 1.90-1.40 (m, 6 H) 1.09 (t, J = 7.3 Hz, 3 H); ,3C NMR (DMSO-d6, 75 MHz) 172.9, 172.2, 153.0, 136.2, 105.4, 60.2, 56.2, 56.0, 51.8, 49.4, 43.1, 28.5, 26.8, 25.3, 21.0, 12.8; 13C NMR (CD3OD, 75 MHz) 175.4, 174.5, 154.9, 137.5, 106.8, 61.5, 57.1, 53.9, 52.1, 45.2, 29.9, 28.2, 26.8, 22.3, 13.2; HRMS (FAB): (M-H)- calcd: 364.1760, meas: 364.1774. Anal. Calcd for C,9H2706: C, 62.45; H, 7.45; N, 3.83. Found: C, 62.32; H, 7.61 ; N, 3.88.

Reference： [1]Patent: CN109734655,2019,A .Location in patent: Paragraph 0030; 0047-0049
[2]Patent: WO2012/103279,2012,A2 .Location in patent: Page/Page column 12-13
[3]Patent: WO2019/126344,2019,A1

3
[ 951-82-6 ]
[ 195202-08-5 ]

Reference： [1]Patent: WO2012/103279,2012,A2
[2]Patent: CN109734655,2019,A

4
[ 195202-06-3 ]
[ 195202-08-5 ]

Yield	Reaction Conditions	Operation in experiment
48.5%	With Cinchonidin; In acetonitrile; at 20℃;	Cpd8 (408g, 1.6mol), cinchonidine (473g 1 · 6mol) was dissolved in CH3CN 6L, heated to reflux, refluxed, heated off, naturally cooled to room temperature, a large amount of white solid precipitated, after standing overnight Filtration, the obtained white solid was further added to CH3CN 5.7 L, and the mixture was refluxed and filtered, and then filtered, and CH3CN (4.9 L, 4.9 L) was added twice, measuring ee value;After the treatment, the solid obtained by the last filtration was added to 1 L of dichloromethane and 1 L of water, acidified with concentrated HCl to pH = 2, extracted, extracted with water three times, and the organic phase was separated; the organic phase was washed twice with 1N HCl solution. Combine the organic phase with 10% NaHCO3The solution was washed once, separated, dried and concentrated; 1 L of n-hexane was added, stirred overnight, filtered and dried to give a white solid Cpd9' (200 g, yield 48.5%).
21%		(lg) Step 7. Synthesis of (S)-2-(3,4,5-Trimethoxyphenyl)butyric acid (AP17360). AP14900 AP17360[195202-08-5]AP14900 (500 g, 1.97 moles) and (-)-cinchonidine (580 g, 1.97 moles) were charged into a 10 L reactor equipped with mechanical agitation. Acetonitrile (7500 mL) was added and the mixture heated to reflux for 30 minutes. The homogeneous solution was allowed to cool to room temperature with concomitant formation of salts. The solids were then filtered and the crystallization procedure was carried out an additional five times utilizing acetonitrile (7000, 7000, 6500, 6500, and 5000 mL) as solvent. The diastereomeric salt was then suspended in water (1400 mL) and dichloromethane (600 mL) and the solution was agitated until all salt was dissolved. The agitated mixture was adjusted to pH 2 by the addition of concentrated HCl, the organic layer was separated and the aqueous layer extracted with a further amount of CH2C12 (2 300 mL). The combined organic layers were then washed with a 1 N HCl solution (2 200 mL) to remove any remaining (-)-cinchonidine. These acid washings were then reextracted with CH2C12 (100 mL) and all CH2C12 solutions were combined. The combined organic solutions were washed with a 10% aqueous NaHC03 solution (200 mL), dried over anhydrous MgS04, concentrated on a rotary evaporator to a volume of -250 mL, and then hexane was added (500 mL). The solution was heated and cooled and an additional portion of hexane (200 mL) was added. The solution was then concentrated on a rotary evaporator until solids appeared and was allowed to sit overnight. The resultant solids were filtered, triturated with hexane (2 300 mL), and placed in a vacuum oven at 50 'C for 84 hours to afford product (105.0 g, 21%) as an off-white solid: [a]22D +54.8 (c = 1.07, MeOH, 30 min, 99.1% ee material); NMR (DMSO-d6, 300 MHz) 6.34 (s, 2 H), 3.52 (s, 6 H), 3.40 (s, 3 H), 3.11 (t, J = 7.6 Hz, 1 H) 1.76-1.64 (m, 1 H), 1.46-1.36 (m, 1 H), 0.60 (t, J = 7.3 Hz, 3 H); l3C NMR (DMSO- d6, 75 MHz) 175.1, 153.1, 136.9, 135.8, 105.4, 60.3, 56.2, 53.1, 26.7, 12.4. Anal. Calcd for C,3H1805: C, 61.41 ; H, 7.13. Found: C, 61.47; H, 7.20.

Reference： [1]Patent: CN109734655,2019,A .Location in patent: Paragraph 0030; 0044-0046
[2]Patent: WO2012/103279,2012,A2 .Location in patent: Page/Page column 11-12

5
[ 1392284-67-1 ]
[ 195202-08-5 ]

Yield	Reaction Conditions	Operation in experiment
		(3b) Chiral s nthesis of AP17360.A solution of the amide (0.5 g, 0.0012 mol) in dioxane (6 mL) was slowly added to a cooled (0 C) solution of 4.5 M ¾S04 (6 mL). When the addition was complete, the mixture was refluxed for 2 hours. The reaction was basified carefully with NaOH to pH 12, and washed with EtOAc twice. The combined organic layer was then dried and evaporated to recover the pseudoephedrine side product as an off white solid (0.17g ca. 85% purity). The aqueous layer was then carefully acidified to pH 3 and extracted with EtOAc. Drying the organic layer over MgS04, filtration, and evaporation of the organic solvent afforded a crude material (0.33g).

Reference： [1]Patent: WO2012/103279,2012,A2 .Location in patent: Page/Page column 15

6
[ 247118-51-0 ]
[ 195202-08-5 ]

Reference： [1]Patent: WO2012/103279,2012,A2

7
[ 195202-08-5 ]
[ 195202-03-0 ]
[ 195202-26-7 ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 11993 - 11997
Angew. Chem.,2018,vol. 130,p. 12169 - 12173,5
[2]Patent: US9096844,2015,B2 .Location in patent: Page/Page column 19-22

8
[ 951-82-6 ]
N<SUP>1</SUP>,N<SUP>3</SUP>-bis((R)-1-phenyl-2-(piperidin-1-yl)ethyl)propane-1,3-diamine [ No CAS ]
[ 75-03-6 ]
[ 195202-08-5 ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 6050 - 6055

9
[ 195202-08-5 ]
[ 914805-33-7 ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 6050 - 6055

10
[ 195202-08-5 ]
(S)-2-(3,4,5-trimethoxyphenyl)butanoyl chloride [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 6050 - 6055

11
[ 195202-08-5 ]
[ 195202-09-6 ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 6050 - 6055

12
[ 195202-08-5 ]
(R)-1-(3-((19-(4-((2,4-diaminopyrimidin-5-yl)methyl)-2,6-dimethoxyphenoxy)-2,18-dioxo-7,10,13-trioxa-3,17-diazanonadecyl)oxy)phenyl)-3-(3,4-dimethoxyphenyl)propyl (S)-1-((S)-2-(3,4,5-trimethoxyphenyl)butanoyl)piperidine-2-carboxylate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 11993 - 11997
Angew. Chem.,2018,vol. 130,p. 12169 - 12173,5

13
[ 195202-08-5 ]
2-(3-((R)-3-(3,4-dimethoxyphenyl)-1-(((S)-1-((S)-2-(3,4,5-trimethoxyphenyl)butanoyl)piperidine-2-carbonyl)oxy)propyl)phenoxy)acetic acid [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 11993 - 11997
Angew. Chem.,2018,vol. 130,p. 12169 - 12173,5

14
[ 195202-08-5 ]
[ 18650-39-0 ]
C₂₀H₂₉NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2-chloro-1-methyl-pyridinium iodide; triethylamine; In dichloromethane; at 12 - 25℃;	(2S)-2-(3,4,5-Trimethoxyphenyl)butanoic acid 9 (93.0 g, 0.37 mol), Methyl (2S)- piperidinecarboxylate hydrochloride 11 (69.0 g, 0.38 mol, 1.1 eq.) and 2-chloro-1-methylpyridinium iodide (117.0 g, 0.46 mol, 1.3 eq.) were dissolved in DCM (720 ml_, 8.0 vol.) and cooled to 12 C. To the reaction mixture was added a solution of triethylamine (111.0 g, 1.10 mol, 3.0 eq.) in DCM (180 ml_, 2.0 vol.) while maintaining the internal temperature below 25 C. The reaction was then allowed to stir for 3-4 hours at 22 C. [IPC HPLC (C18: ACN/H20 10-90%, 20 min, 1 mL/min) 9: rrt 0.53 min, Intermediate ester: rrt 0.69, 14: rrt 0.58] Upon completion, the DCM was removed by rotary evaporation and exchanged for MeOH (225 ml_, 2.5 vol.). To the methanolic solution was added a solution of UOH.H2O (77.0 g, 1.83 mol, 5.0 eq.) in Dl water (225 ml_, 2.5 vol.) and the reaction was stirred for 12 hours at 22 C. Upon completion, as determined by IPC, additional water (180 ml_, 2.0 vol.) was added and the solution is vacuum distilled to remove methanol. EtOAc (450 ml_, 5.0 vol.) was added and the biphasic solution stirred vigorously for 10 minutes after which the phases were separated. The aqueous layer containing the product was removed and the organic phase was washed again with water (180 ml_, 2.0 vol.) and 10% NaHCC>3 sol. (360 ml_, 4.0 vol.). The combined aqueous layers were cooled to 4 C. A solution of 5M HCI was slowly added until the pH 4. The resulting slurry was stirred at 4 C for 3 hours then the solid was collected by vacuum filtration. The crude 14 (117.0 g, 0.32 mol) was dissolved in EtOH (1080 ml_, 12.0 vol.), heated and maintained at 50 C for 30 minutes. The ethanolic solution was then cooled to 0 C over 6 hours. The resulting crystalline solid is collected by vacuum filtration and washed with cold EtOH (90 ml_, 1.0 vol.). The product 14 (87.5 g, 0.24 mol, 66% yield) was obtained a colorless crystalline solid.Reverse phase HPLC analysis showed crystalline 14 (11.64 min) to be excellent purity with no detectable impurities. Chiral HPLC analysis shows crystalline 14 (32.58 min) to be excellent purity with no detectable chiral impurities.

Reference： [1]Patent: WO2019/126344,2019,A1 .Location in patent: Page/Page column 137; 138

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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

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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. 195202-08-5 ] {[proInfo.proName]}

Quality Control of [ 195202-08-5 ]

Related Doc. of [ 195202-08-5 ]

Product Details of [ 195202-08-5 ]

Calculated chemistry of [ 195202-08-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 195202-08-5 ]

Application In Synthesis of [ 195202-08-5 ]

[ 195202-08-5 ] Synthesis Path-Upstream 1~5

[ 195202-08-5 ] Synthesis Path-Downstream 1~14

Related Functional Groups of [ 195202-08-5 ]

Aryls

Ethers

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 195202-08-5 ]