Sodium Chloride → N-acetyl-DL-cysteinyl-L-proline

HRID 65859Notes

Reaction equation

HRID 65859 reaction equation
[C:1]([NH:4][CH:5]([C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=[O:16])=[O:12])[CH2:6][S:7]C(=O)C)(=[O:3])[CH3:2].[Cl-].[Na+]>O.N>[C:1]([NH:4][CH:5]([C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=[O:16])=[O:12])[CH2:6][SH:7])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 12774422N,S-diacetyl-DL-cysteinyl-L-proline

Product 1

HCID 14181605N-acetyl-DL-cysteinyl-L-proline

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 962WaterSolvent

Procedure

N,S-Diacetyl-DL-cysteinyl-L-proline (0.3 g) is dissolved in a mixture of water (4 ml) and concentrated ammonia (4 ml) under a blanket of argon. The solution is stored for 30 minutes at room temperature, saturated with sodium chloride and extracted with ethyl acetate and chloroform. The organic layers are pooled and concentrated to dryness in vacuo to obtain N-acetyl-DL-cysteinyl-L-proline, yield 0.1 g, Rf =0.25 (silica gel; benzene:acetic acid, 75:25).

Workup

  1. extractionextracted with ethyl acetate and chloroform
  2. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-ad3e708911514574abd75de3d8c441a0
Source dataset
uspto-grants-1978_12
Patent number
US04129571

Reaction notes

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