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

HRID 2071388Notes

Reaction equation

HRID 2071388 reaction equation
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]

Participants

4

Reactant 1

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

Product 1

HCID 228203034-mercaptobutanoyl-L-proline

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 962WaterSolvent2×

Procedure

1-(4-Benzylthiobutanoyl)-L-proline (1.08 g.) is dissolved in a mixture of water (4 ml.) and concentrated ammonia (2.7 ml.). After 1 hour stirring at room temperature, the mixture is diluted with water, filtered, extracted with ethyl acetate, and the aqueous phase was concentrated in vacuo. This ammonium salt of 1-(4-mercaptobutanoyl)-L-proline is purified by ion exchange chromatography on a column of diethyl-aminoethyl-Sephadex(cross linked dextran) with a gradient of ammonium bicarbonate, yield 0.7 g. The ammonium salt is dissolved in water (2ml.) 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.

Workup

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

Sources & evidence

ORD record
ord-16a80f7264324dcd8d298949e8ae976e
Source dataset
uspto-grants-1977_09
Patent number
US04046889

Reaction notes

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