1-[2-acetoxymethyl-3-(acetylthio)propanoyl]-L-proline → 1-(2-hydroxymethyl-3-mercaptopropanoyl)-L-proline

HRID 1252828Notes

Reaction equation

HRID 1252828 reaction equation
C([O:4][CH2:5][CH:6]([CH2:17][S:18]C(=O)C)[C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8])(=O)C>O.N>[OH:4][CH2:5][CH:6]([CH2:17][SH:18])[C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8]

Participants

4

Reactant 1

HCID 537381251-[2-acetoxymethyl-3-(acetylthio)propanoyl]-L-proline

Product 1

HCID 540969871-(2-hydroxymethyl-3-mercaptopropanoyl)-L-proline

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 962WaterSolvent

Procedure

N-[2-acetoxymethyl-3-(acetylthio)propanoyl]-L-proline (1.5 g) is dissolved in a mixture of water (12 ml) and concentrated ammonia (12 ml) under a blanket of argon. After one hour, the reaction mixture is concentrated to ca. dryness, diluted with water and the solution applied to a column of cation exchange resin (Dowex 50) in the hydrogen cycle. The water eluate is concentrated to small volume and freeze-dried to yield N-(2-hydroxymethyl-3-mercaptopropanoyl)-L-proline.

Workup

  1. concentrationthe reaction mixture is concentrated to ca. dryness
  2. additiondiluted with water
  3. concentrationThe water eluate is concentrated to small volume
  4. customfreeze-dried

Sources & evidence

ORD record
ord-e33bbfcb94314d99850c5fbe89fa142e
Source dataset
uspto-grants-1988_05
Patent number
US04745124

Reaction notes

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