1-(2-acetylthiomethyl-5-aminopentanoyl)-L-proline trifluoroacetate → 1-(5-Amino-2-mercaptomethylpentanoyl)-L-proline

HRID 261329Notes

Reaction equation

HRID 261329 reaction equation
FC(F)(F)C(O)=O.C([S:11][CH2:12][CH:13]([CH2:24][CH2:25][CH2:26][NH2:27])[C:14]([N:16]1[CH2:23][CH2:22][CH2:21][C@H:17]1[C:18]([OH:20])=[O:19])=[O:15])(=O)C>O.N>[NH2:27][CH2:26][CH2:25][CH2:24][CH:13]([CH2:12][SH:11])[C:14]([N:16]1[CH2:23][CH2:22][CH2:21][C@H:17]1[C:18]([OH:20])=[O:19])=[O:15]

Participants

4

Reactant 1

HCID 867360071-(2-acetylthiomethyl-5-aminopentanoyl)-L-proline trifluoroacetate

Product 1

HCID 127697271-(5-Amino-2-mercaptomethylpentanoyl)-L-proline

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 962WaterSolvent

Procedure

1-(2-Acetylthiomethyl-5-aminopentanoyl)-L-proline trifluoroacetate (1 g) is dissolved in a mixture of water (12 ml) and concentrated ammonia (12 ml) under a blanket of argon. The solution is stored twenty minutes at room temperature concentrated to 5 ml and applied to a column of Dowex 50 ion exchange resin in the hydrogen cycle. The column is washed with water and 1-(5-amino-2-mercaptomethylpentanoyl)-L-proline is eluted with a buffer of pyridine-acetic acid at pH 6.5.

Workup

  1. waitThe solution is stored twenty minutes at room temperature
  2. concentrationconcentrated to 5 ml
  3. washThe column is washed with water and 1-(5-amino-2-mercaptomethylpentanoyl)-L-proline
  4. washis eluted with a buffer of pyridine-acetic acid at pH 6.5

Sources & evidence

ORD record
ord-3c55877c10a144a594564fef7d30bca6
Source dataset
uspto-grants-1979_08
Patent number
US04165320

Reaction notes

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