Product Name

  • Name

    (S)-(-)-3-(Benzoylthio)-2-methylpropanoic acid

  • EINECS 276-764-6
  • CAS No. 72679-02-8
  • Article Data5
  • CAS DataBase
  • Density 1.249 g/cm3
  • Solubility
  • Melting Point 61-63oC
  • Formula C11H12O3S
  • Boiling Point 367.5 °C at 760 mmHg
  • Molecular Weight 224.28
  • Flash Point 176 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 72679-02-8 ((S)-(-)-3-(Benzoylthio)-2-methylpropanoic acid)
  • Hazard Symbols
  • Synonyms 3-benzoylsulfanyl-2-methyl-propanoic acid;(S)-3-(Benzoylthio)-2-methylpropionic acid;S-(-)-3-benzoylthio-2-methylpropionic acid;S-(-)-3-benzoylthio-2-methyl propionic acid;
  • PSA 79.67000
  • LogP 2.28070

Synthetic route

benzoyl chloride
98-88-4

benzoyl chloride

(2S)-2-methyl-3-sulfanylpropanoic acid
75172-11-1

(2S)-2-methyl-3-sulfanylpropanoic acid

(2S)-3-(benzoylthio)-2-methylpropionic acid
72679-02-8

(2S)-3-(benzoylthio)-2-methylpropionic acid

Conditions
ConditionsYield
With sodium hydroxide In water Inert atmosphere;71.9%
(D)-3-(Benzoylthio)-2-methylpropanoic acid
74431-50-8

(D)-3-(Benzoylthio)-2-methylpropanoic acid

(2S)-3-(benzoylthio)-2-methylpropionic acid
72679-02-8

(2S)-3-(benzoylthio)-2-methylpropionic acid

4-nitro-phenol
100-02-7

4-nitro-phenol

(2S)-3-(benzoylthio)-2-methylpropionic acid
72679-02-8

(2S)-3-(benzoylthio)-2-methylpropionic acid

4-nitrophenyl (2S)-3-benzoylthio-2-methylpropionate

4-nitrophenyl (2S)-3-benzoylthio-2-methylpropionate

Conditions
ConditionsYield
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

toluene-ethyl acetate

potassium tert-butylate
865-47-4

potassium tert-butylate

(4S)-1-methyl-2-oxoimidazolidine-4-carboxylic acid t-butyl ester
83056-79-5

(4S)-1-methyl-2-oxoimidazolidine-4-carboxylic acid t-butyl ester

(2S)-3-(benzoylthio)-2-methylpropionic acid
72679-02-8

(2S)-3-(benzoylthio)-2-methylpropionic acid

(2S)-3-benzoylthio-2-methylpropionyl chloride
72679-01-7

(2S)-3-benzoylthio-2-methylpropionyl chloride

tert.-butyl (4S)-1-methyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate

tert.-butyl (4S)-1-methyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate

Conditions
ConditionsYield
With thionyl chloride In tetrahydrofuran; ethyl acetate73.9%
...Expand
toluene-ethyl acetate

toluene-ethyl acetate

potassium tert.-butoxide, (2S)-3-benzoylthio-2-methylpropionyl chloride

potassium tert.-butoxide, (2S)-3-benzoylthio-2-methylpropionyl chloride

(S)-1-ethyl-2-oxoimidazolidine-4-carboxylic acid tert-butyl ester

(S)-1-ethyl-2-oxoimidazolidine-4-carboxylic acid tert-butyl ester

(2S)-3-(benzoylthio)-2-methylpropionic acid
72679-02-8

(2S)-3-(benzoylthio)-2-methylpropionic acid

tert-butyl (4S)-1-ethyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate

tert-butyl (4S)-1-ethyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate

Conditions
ConditionsYield
With thionyl chloride In tetrahydrofuran71.3%
...Expand
toluene-ethyl acetate

toluene-ethyl acetate

potassium tert.-butoxide, (2S)-3-benzoylthio-2-methylpropionyl chloride

potassium tert.-butoxide, (2S)-3-benzoylthio-2-methylpropionyl chloride

(2S)-3-(benzoylthio)-2-methylpropionic acid
72679-02-8

(2S)-3-(benzoylthio)-2-methylpropionic acid

tert.-butyl (4S)-1-benzyl-2-oxo-imidazolidine-4-carboxylate
83057-01-6

tert.-butyl (4S)-1-benzyl-2-oxo-imidazolidine-4-carboxylate

tert.-butyl (4S)-1-benzyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate
83057-02-7

tert.-butyl (4S)-1-benzyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate

Conditions
ConditionsYield
With thionyl chloride In tetrahydrofuran70.7%
...Expand
toluene-ethyl acetate

toluene-ethyl acetate

potassium tert.-butoxide, (2S)-3-benzoylthio-2-methylpropionyl chloride

potassium tert.-butoxide, (2S)-3-benzoylthio-2-methylpropionyl chloride

tert.-butyl (4S)-1-n-butyl-2-oxo-imidazolidine-4-carboxylate

tert.-butyl (4S)-1-n-butyl-2-oxo-imidazolidine-4-carboxylate

(2S)-3-(benzoylthio)-2-methylpropionic acid
72679-02-8

(2S)-3-(benzoylthio)-2-methylpropionic acid

tert.-butyl (4S)-1-n-butyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate

tert.-butyl (4S)-1-n-butyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate

Conditions
ConditionsYield
With thionyl chloride In tetrahydrofuran68.4%
...Expand
(4R)-2-(2-Thienyl)-1,3-thiazolidine-4-carboxylic acid
201942-94-1

(4R)-2-(2-Thienyl)-1,3-thiazolidine-4-carboxylic acid

(2S)-3-(benzoylthio)-2-methylpropionic acid
72679-02-8

(2S)-3-(benzoylthio)-2-methylpropionic acid

(4R)-3-[(2S)-S-Benzoyl-3-mercapto-2-methylpropanoyl]-2-(2-thienyl)-4-thiazolidinecarboxylic acid
72678-60-5

(4R)-3-[(2S)-S-Benzoyl-3-mercapto-2-methylpropanoyl]-2-(2-thienyl)-4-thiazolidinecarboxylic acid

Conditions
ConditionsYield
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-methylpropionic acid

(2S)-3-benzoylthio-2-methylpropionyl chloride
72679-01-7

(2S)-3-benzoylthio-2-methylpropionyl chloride

Conditions
ConditionsYield
With thionyl chloride
With thionyl chloride
(2S)-3-(benzoylthio)-2-methylpropionic acid
72679-02-8

(2S)-3-(benzoylthio)-2-methylpropionic acid

(S)-3-(benzoylthio)-2-methylpropanoylchloride
74654-91-4

(S)-3-(benzoylthio)-2-methylpropanoylchloride

Conditions
ConditionsYield
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

(2S)-3-(benzoylthio)-2-methylpropionic acid

N-[(2S)-3-benzoylthio-2-methylpropionyl]-S-(4-dimethylamino)benzyl-L-cysteine
183121-03-1

N-[(2S)-3-benzoylthio-2-methylpropionyl]-S-(4-dimethylamino)benzyl-L-cysteine

Conditions
ConditionsYield
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

(2S)-3-(benzoylthio)-2-methylpropionic acid

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

1-<(S)-3-(benzoylthio)-2-methyl-1-oxopropyl>indoline-2-carboxylic acid

Conditions
ConditionsYield
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

(2S)-3-(benzoylthio)-2-methylpropionic acid

(-)-(R)-1-<(S)-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

Conditions
ConditionsYield
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

(2S)-3-(benzoylthio)-2-methylpropionic acid

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

(+)-(S)-1-<(R)-(3-benzoylthio)-2-methyl-1-oxopropyl>indoline-2-carboxylic acid

Conditions
ConditionsYield
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

(2S)-3-(benzoylthio)-2-methylpropionic acid

(S)-1-(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

Conditions
ConditionsYield
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

(2S)-3-(benzoylthio)-2-methylpropionic acid

(S)-1-((S)-3-Benzoylsulfanyl-2-methyl-propionyl)-5-ethyl-2,3-dihydro-1H-indole-2-carboxylic acid
84117-84-0

(S)-1-((S)-3-Benzoylsulfanyl-2-methyl-propionyl)-5-ethyl-2,3-dihydro-1H-indole-2-carboxylic acid

Conditions
ConditionsYield
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

(2S)-3-(benzoylthio)-2-methylpropionic acid

(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

(R)-2-((S)-3-Benzoylsulfanyl-2-methyl-propionyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid benzyl ester

Conditions
ConditionsYield
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

(cis)-4-(phenylthio)-L-proline

oxalyl dichloride
79-37-8

oxalyl dichloride

(2S)-3-(benzoylthio)-2-methylpropionic acid
72679-02-8

(2S)-3-(benzoylthio)-2-methylpropionic acid

zofenopril
81872-10-8

zofenopril

Conditions
ConditionsYield
With sodium hydroxide; N,N-dimethyl-formamide In dichloromethane; 2-methylpropyl acetate
...Expand
trans-4-phenylthio-L-proline, hydrochloride

trans-4-phenylthio-L-proline, hydrochloride

(2S)-3-(benzoylthio)-2-methylpropionic acid
72679-02-8

(2S)-3-(benzoylthio)-2-methylpropionic acid

zofenopril
81872-10-8

zofenopril

Conditions
ConditionsYield
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℃;

(S)-(-)-3-(Benzoylthio)-2-methylpropanoic acid Chemical Properties

IUPAC Name: (2S)-3-Benzoylsulfanyl-2-methylpropanoic acid 
Synonyms of (S)-(-)-3-(Benzoylthio)-2-methylpropanoic acid (CAS NO.72679-02-8): (2S)-3-Benzoylsulfanyl-2-methylpropanoic acid ; (S)-3-(Benzoylthio)-2-methylpropionic acid 
CAS NO: 72679-02-8
Molecular Formula: C11H12O3S 
Molecular Weight: 224.28 
Molecular Structure:
EINECS  276-764-6
H bond acceptors:  3 
H bond donors:  1 
Freely Rotating Bonds:  5 
Polar Surface Area: 68.67 Å2 
Index of Refraction: 1.579 
Molar Refractivity: 59.69 cm3 
Molar Volume: 179.4 cm3 
Surface Tension: 51.8 dyne/cm 
Density: 1.249 g/cm3 
Flash Point: 176 °C 
Enthalpy of Vaporization:  64.78 kJ/mol 
Boiling Point: 367.5 °C at 760 mmHg 
Vapour Pressure:  4.77E-06 mmHg at 25°C 
SMILES: O=C(O)C(CSC(=O)c1ccccc1)C  
InChI: InChI=1/C11H12O3S/c1-8(10(12)13)7-15-11(14)9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,12,13)
InChIKey: BCAYPPFBOJCRPN-UHFFFAOYAC 
Std. InChI: InChI=1S/C11H12O3S/c1-8(10(12)13)7-15-11(14)9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,12,13) 
Std. InChIKey: BCAYPPFBOJCRPN-UHFFFAOYSA-N

(S)-(-)-3-(Benzoylthio)-2-methylpropanoic acid Uses

 (S)-(-)-3-(Benzoylthio)-2-methylpropanoic acid (CAS NO.72679-02-8) is used as pharmaceutical intermediate.

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