Potassium Carbonate → 1-[2-benzoylthio-3-methoxybutanoyl]L-proline

HRID 1252829Notes

Reaction equation

HRID 1252829 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].Br[CH:10]([CH:14]([O:16][CH3:17])[CH3:15])[C:11](Cl)=[O:12].[C:18]([OH:26])(=[S:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>[OH-].[Na+]>[C:18]([S:25][CH:10]([CH:14]([O:16][CH3:17])[CH3:15])[C:11]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])=[O:12])(=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 130170472-Bromo-3-methoxybutyryl chlorideHCID 178526132HCID 178526132, compound

Product 1

HCID 186324661-[2-benzoylthio-3-methoxybutanoyl]L-proline

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of L-proline (5.75 g) in N sodium hydroxide (50 ml) chilled in an ice bath, 2N sodium hydroxide (25 ml) and 2-bromo-3-methoxybutyric acid chloride [obtained from 2-bromo-3-methoxybutyric acid [J. Am. Chem. Soc., 71, 1096, (1949)] and thionyl chloride] (10.7 g) are added, with vigorous stirring. After three hours, thiobenzoic acid (7.5 g) and potassium carbonate (4.8 g) are added and the mixture is stirred at room temperature overnight. The reaction mixture is acidified and extracted with ethyl acetate. The organic layer is concentrated to dryness and the residue is chromatographed on a column of silica gel with benzene-acetic acid to yield N-[2-benzoylthio-3-methoxybutanoyl]-L-proline.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer is concentrated to dryness
  3. customthe residue is chromatographed on a column of silica gel with benzene-acetic acid

Sources & evidence

ORD record
ord-387804414a1645e685a15f0cb260fcc1
Source dataset
uspto-grants-1988_05
Patent number
US04745124

Reaction notes

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