72679-02-8

Basic information

• Product Name: (S)-(-)-3-(Benzoylthio)-2-methylpropanoic acid
• Synonyms: (S)-3-(benzoylthio)-2-methylpropionic acid;(S)-(-)-3-(Benzoylthio)-2-methylpropanoic acid;(2S)-3-(Benzoylthio)-2-Methylpropanoic Acid;(2S)-3-(benzoylthio)-2-methylpropionic acid, S-(-)-3-benzoylthio-2-methylpropanoic acid, (S)-3-(benzoylthio)isobutyric acid, (2S)-S-benzoyl-3-mercapto-2-methylpropanoyc acid, (-)-(S)-3-(benzoylthio)-2-methylpropanoic acid, (S)-(-)-3-benzoylthio-2-methylpropanoic acid, (2S)-3-benzoylthio-2-methylpropionic acid;(S)-3-(Benzoylthio)-2-methylpropionic Acid
• CAS NO: 72679-02-8
• Molecular Formula: C₁₁H₁₂O₃S
• Molecular Weight: 224.28
• EINECS: 276-764-6
• Product Categories: Aromatics;Chiral Reagents;Sulfur & Selenium Compounds
• Mol File: 72679-02-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 61-63°C
• Boiling Point: 367.5 °C at 760 mmHg
• Flash Point: 176 °C
• Appearance: /
• Density: 1.249 g/cm³
• Vapor Pressure: 1.29E-06mmHg at 25°C
• Refractive Index: 1.62
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: Chloroform, Ethanol, Methanol
• PKA: 4.20±0.10(Predicted)
• CAS DataBase Reference: (S)-(-)-3-(Benzoylthio)-2-methylpropanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-3-(Benzoylthio)-2-methylpropanoic acid(72679-02-8)
• EPA Substance Registry System: (S)-(-)-3-(Benzoylthio)-2-methylpropanoic acid(72679-02-8)

Safety Data

• Hazardous Substances Data: 72679-02-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Captopril intermediate.

InChI:InChI=1/C10H11NO3S/c11-8(9(12)13)6-15-10(14)7-4-2-1-3-5-7/h1-5,8H,6,11H2,(H,12,13)/t8-/m0/s1

Synthetic route

benzoyl chloride (98-88-4) + (2S)-2-methyl-3-sulfanylpropanoic acid (75172-11-1) → (2S)-3-(benzoylthio)-2-methylpropionic acid (72679-02-8)

Conditions	Yield
With sodium hydroxide In water Inert atmosphere;	71.9%

(D)-3-(Benzoylthio)-2-methylpropanoic acid (74431-50-8) → (2S)-3-(benzoylthio)-2-methylpropionic acid (72679-02-8)

4-nitro-phenol (100-02-7) + (2S)-3-(benzoylthio)-2-methylpropionic acid (72679-02-8) → 4-nitrophenyl (2S)-3-benzoylthio-2-methylpropionate

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 4h;	87%
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h;
In dichloromethane

toluene-ethyl acetate + potassium tert-butylate (865-47-4) + (4S)-1-methyl-2-oxoimidazolidine-4-carboxylic acid t-butyl ester (83056-79-5) + (2S)-3-(benzoylthio)-2-methylpropionic acid (72679-02-8) + (2S)-3-benzoylthio-2-methylpropionyl chloride (72679-01-7) → tert.-butyl (4S)-1-methyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate

Conditions	Yield
With thionyl chloride In tetrahydrofuran; ethyl acetate	73.9%

toluene-ethyl acetate + potassium tert.-butoxide, (2S)-3-benzoylthio-2-methylpropionyl chloride + (S)-1-ethyl-2-oxoimidazolidine-4-carboxylic acid tert-butyl ester + (2S)-3-(benzoylthio)-2-methylpropionic acid (72679-02-8) → tert-butyl (4S)-1-ethyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate

Conditions	Yield
With thionyl chloride In tetrahydrofuran	71.3%

toluene-ethyl acetate + potassium tert.-butoxide, (2S)-3-benzoylthio-2-methylpropionyl chloride + (2S)-3-(benzoylthio)-2-methylpropionic acid (72679-02-8) + tert.-butyl (4S)-1-benzyl-2-oxo-imidazolidine-4-carboxylate (83057-01-6) → tert.-butyl (4S)-1-benzyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate (83057-02-7)

Conditions	Yield
With thionyl chloride In tetrahydrofuran	70.7%

toluene-ethyl acetate + potassium tert.-butoxide, (2S)-3-benzoylthio-2-methylpropionyl chloride + tert.-butyl (4S)-1-n-butyl-2-oxo-imidazolidine-4-carboxylate + (2S)-3-(benzoylthio)-2-methylpropionic acid (72679-02-8) → tert.-butyl (4S)-1-n-butyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate

Conditions	Yield
With thionyl chloride In tetrahydrofuran	68.4%

(4R)-2-(2-Thienyl)-1,3-thiazolidine-4-carboxylic acid (201942-94-1) + (2S)-3-(benzoylthio)-2-methylpropionic acid (72679-02-8) → (4R)-3-[(2S)-S-Benzoyl-3-mercapto-2-methylpropanoyl]-2-(2-thienyl)-4-thiazolidinecarboxylic acid (72678-60-5)

Conditions	Yield
With triethylamine; isobutyl chloroformate 1) tetrahydrofuran, RT, 10 min, 2) water, RT, 30 min; Yield given. Multistep reaction;

(2S)-3-(benzoylthio)-2-methylpropionic acid (72679-02-8) → (2S)-3-benzoylthio-2-methylpropionyl chloride (72679-01-7)

Conditions	Yield
With thionyl chloride
With thionyl chloride

(2S)-3-(benzoylthio)-2-methylpropionic acid (72679-02-8) → (S)-3-(benzoylthio)-2-methylpropanoylchloride (74654-91-4)

Conditions	Yield
With pyridine; thionyl chloride for 7h; Ambient temperature;
With thionyl chloride; triethylamine In calcium chloride
With thionyl chloride In toluene Large scale reaction;

(2S)-3-(benzoylthio)-2-methylpropionic acid (72679-02-8) → N-[(2S)-3-benzoylthio-2-methylpropionyl]-S-(4-dimethylamino)benzyl-L-cysteine (183121-03-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: DCC / CH2Cl2 / 4 h / 20 °C 2: Et3N / dimethylformamide; CH2Cl2 / 48 h / 20 °C View Scheme

(2S)-3-(benzoylthio)-2-methylpropionic acid (72679-02-8) → 1-<(S)-3-(benzoylthio)-2-methyl-1-oxopropyl>indoline-2-carboxylic acid (78701-25-4, 78701-28-7, 78779-25-6, 78779-26-7, 78779-27-8, 78779-28-9, 106517-52-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2, pyridine / 7 h / Ambient temperature 2: Et3N / CH2Cl2 / 2.75 h / 0 - 20 °C View Scheme

(2S)-3-(benzoylthio)-2-methylpropionic acid (72679-02-8) → (-)-(R)-1-<(S)-3-(benzoylthio)-2-methyl-1-oxopropyl>indoline-2-carboxylic acid (78779-28-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: SOCl2, pyridine / 7 h / Ambient temperature 2: Et3N / CH2Cl2 / 2.75 h / 0 - 20 °C View Scheme

(2S)-3-(benzoylthio)-2-methylpropionic acid (72679-02-8) → (+)-(S)-1-<(R)-(3-benzoylthio)-2-methyl-1-oxopropyl>indoline-2-carboxylic acid (78779-26-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2, pyridine / 7 h / Ambient temperature 2: Et3N / CH2Cl2 / 2.75 h / 0 - 20 °C View Scheme

(2S)-3-(benzoylthio)-2-methylpropionic acid (72679-02-8) → (S)-1-(3-Benzoylsulfanyl-2-methyl-propionyl)-5-ethyl-2,3-dihydro-1H-indole-2-carboxylic acid (84117-84-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2, pyridine / 7 h / Ambient temperature 2: 1.) Et3N, 2.) 5 percent aq. KHSO4 / 1.) CH2Cl2, 0 deg C, 15 min, RT, 2.5 h View Scheme

(2S)-3-(benzoylthio)-2-methylpropionic acid (72679-02-8) → (S)-1-((S)-3-Benzoylsulfanyl-2-methyl-propionyl)-5-ethyl-2,3-dihydro-1H-indole-2-carboxylic acid (84117-84-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: SOCl2, pyridine / 7 h / Ambient temperature 2: 1.) Et3N, 2.) 5 percent aq. KHSO4 / 1.) CH2Cl2, 0 deg C, 15 min, RT, 2.5 h View Scheme

(2S)-3-(benzoylthio)-2-methylpropionic acid (72679-02-8) → (R)-2-((S)-3-Benzoylsulfanyl-2-methyl-propionyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid benzyl ester (87022-29-5, 87022-30-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride 2: triethyl amine / tetrahydrofuran / 4 h / 5 - 10 °C View Scheme

(cis)-4-(phenylthio)-L-proline + oxalyl dichloride (79-37-8) + (2S)-3-(benzoylthio)-2-methylpropionic acid (72679-02-8) → zofenopril (81872-10-8)

Conditions	Yield
With sodium hydroxide; N,N-dimethyl-formamide In dichloromethane; 2-methylpropyl acetate

trans-4-phenylthio-L-proline, hydrochloride + (2S)-3-(benzoylthio)-2-methylpropionic acid (72679-02-8) → zofenopril (81872-10-8)

Conditions	Yield
Stage #1: trans-4-phenylthio-L-proline, hydrochloride With triethylamine In toluene at 25 - 30℃; for 1h; Stage #2: (2S)-3-(benzoylthio)-2-methylpropionic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In toluene at 30 - 35℃;

Upstream product

• 74431-50-8 (D)-3-(Benzoylthio)-2-methylpropanoic acid 
• 98-88-4 benzoyl chloride 
• 75172-11-1 (S)-3-mercapto-2-methyl-propionic acid 

Downstream Products

• 72679-01-7 (2S)-3-benzoylthio-2-methylpropionyl chloride 
• 74654-91-4 3-(benzoylthio)-2(S)-methylpropionyl chloride 
• 81872-10-8 zofenopril 
• 87022-29-5 (R)-2-((S)-3-Benzoylsulfanyl-2-methyl-propionyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid benzyl ester 
• 93040-22-3 (S)-N-cyclopentyl-N-<3-(benzoylthio)-2-methyl-1-oxopropyl>glycine tert-butyl ester 
• 72678-60-5 (4R)-3-[(2S)-S-Benzoyl-3-mercapto-2-methylpropanoyl]-2-(2-thienyl)-4-thiazolidinecarboxylic acid 
• 83057-02-7 tert.-butyl (4S)-1-benzyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate 
• 84117-84-0 (S)-1-((S)-3-Benzoylsulfanyl-2-methyl-propionyl)-5-ethyl-2,3-dihydro-1H-indole-2-carboxylic acid 
• 84117-84-0 (S)-1-(3-Benzoylsulfanyl-2-methyl-propionyl)-5-ethyl-2,3-dihydro-1H-indole-2-carboxylic acid 
• 78779-26-7 (+)-(S)-1-<(R)-(3-benzoylthio)-2-methyl-1-oxopropyl>indoline-2-carboxylic acid 
• 78779-28-9 (-)-(R)-1-<(S)-3-(benzoylthio)-2-methyl-1-oxopropyl>indoline-2-carboxylic acid 
• 78701-25-4 1-<(S)-3-(benzoylthio)-2-methyl-1-oxopropyl>indoline-2-carboxylic acid 
• 183121-03-1 N-[(2S)-3-benzoylthio-2-methylpropionyl]-S-(4-dimethylamino)benzyl-L-cysteine 

Relevant articles and documents

Method for preparing S-(-)-Benzoylthio-2-methylpropanoic acid compound

The invention discloses a method for preparing a S-(-)-Benzoylthio-2-methylpropanoic acid compound. S-(-)-3-acetylthio-2-methylpropionic acid as a raw material shown in the formula II is hydrolyzed ina reacting solvent to obtain S-(-)-3-mercapto-2-methylpropionic acid shown in hte formula III, and the S-(-)-3-mercapto-2-methylpropionic acid and benzoyl chloride are subjected to condensation to obtain the S-(-)-Benzoylthio-2-methylpropanoic acid shown in the formula I. The preparation method is easy in operation, the raw materials and accessory materials are low in cost and easy to obtain, thereaction conditions are mild, the yield is high, and the quality is high. (The formula is shown in the description.).

2-OXOIMIDAZOLIDINE DERIVATIVES

A 2-oxoimidazolidine derivative of the formula: STR1 wherein R 1 is lower alkyl or phenyl-lower alkyl and R 2 is lower alkyl or phenyl, and a process for preparation thereof are disclosed. Said 2-oxoimidazolidine derivative (I) or a pharmaceutically acceptable salt thereof is useful as a hypotensive agent.

Synthesis of captopril starting from an optically active β-hydroxy acid

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