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

HRID 263336Notes

Reaction equation

HRID 263336 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 thirty 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-dbc27357b2cd47f797f59e857498db90
Source dataset
uspto-grants-1979_05
Patent number
US04156786

Reaction notes

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