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

HRID 47138노트

반응식

HRID 47138 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매2회

실험 절차

To a solution of L-proline (5.75 g.) in N sodium hydroxide (50 ml.) chilled in an ice bath, 2 N 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 1-[2-benzoylthio-3-methoxybutanoyl]-L-proline.

후처리

  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

출처 및 근거

ORD 기록
ord-8254db017cb94858be0a03ca8d58180b
출처 데이터셋
uspto-grants-1979_11
특허 번호
US04176235

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