1-(4-Benzylthiobutanoyl)-L-proline → 4-mercaptobutanoyl-L-proline

HRID 2419425노트

반응식

HRID 2419425 반응식
C([S:8][CH2:9][CH2:10][CH2:11][C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13])C1C=CC=CC=1>O.N>[SH:8][CH2:9][CH2:10][CH2:11][C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13]

참가 물질

4

반응물 1

HCID 700744061-(4-Benzylthiobutanoyl)-L-proline

생성물 1

HCID 228203034-mercaptobutanoyl-L-proline

시약·촉매·용매 2

HCID 222Ammonia용매HCID 962Water용매2회

실험 절차

1-(4-Benzylthiobutanoyl)-L-proline (1.08 g.) is dissolved in a mixture of water (4 ml.) and concentrated ammonia (2.7 ml.). After one hour stirring at room temperature, the mixture is diluted with water, filtered, extracted with ethyl acetate, and the aqueous phase is concentrated in vacuo. This ammonium salt of 1-(4-mercaptobutanoyl)-L-proline is purified by ion exchange chromatography on a column of diethylaminoethyl-Sephadex(cross linked dextran) with a gradient of ammonium bicarbonate, yield 0.7 g. The ammonium salt is dissolved in water (2 ml.) and applied to a column of Dowex 50 sulfonic acid resin analytical grade in the hydrogen form, and the free acid is eluted with water. The fractions containing the desired material (sulfhydryl reagent and carboxyl reagent positive) are pooled and freeze dried to obtain 1-(4-mercaptobutanoyl)-L-proline. The dicyclohexyl ammonium salt is produced by the procedure of Example 44, m.p. 157°-158°.

후처리

  1. filtrationfiltered
  2. extractionextracted with ethyl acetate
  3. concentrationthe aqueous phase is concentrated in vacuo
  4. customThis ammonium salt of 1-(4-mercaptobutanoyl)-L-proline is purified by ion exchange chromatography on a column of diethylaminoethyl-Sephadex(cross linked dextran) with a gradient of ammonium bicarbonate, yield 0.7 g
  5. dissolutionThe ammonium salt is dissolved in water (2 ml.)
  6. washthe free acid is eluted with water
  7. additionThe fractions containing the desired material (sulfhydryl reagent and carboxyl reagent positive)
  8. customfreeze dried

출처 및 근거

ORD 기록
ord-421c43e433604f05a64c41718604ff78
출처 데이터셋
uspto-grants-1978_08
특허 번호
US04105776

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