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

HRID 262557ノート

反応式

HRID 262557 の反応式
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]

参加物

4

反応物 1

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

生成物 1

HCID 228203034-mercaptobutanoyl-L-proline

試薬・触媒・溶媒 2

HCID 222Ammonia溶媒HCID 962Water溶媒2 回

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-4ac7d0413a6f4971bdc6df5dc271b123
出典データセット
uspto-grants-1979_05
特許番号
US04154840

反応ノート

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