N-Acetyl-L-Cysteine → HCID 57291887, compound

HRID 456383Notes

Reaction equation

HRID 456383 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:20]([NH:23][C@H:24]([C:27]([OH:29])=[O:28])[CH2:25][SH:26])(=[O:22])[CH3:21].CC[O-].[Na+]>C(Cl)(Cl)Cl.CN(C)C=O>[C:20]([NH:23][C@H:24]([C:27]([OH:29])=[O:28])[CH2:25][S:26][C:5](=[O:7])[CH2:4][CH2:3][CH2:2][Br:1])(=[O:22])[CH3:21]

Participants

7

Reactant 4

HCID 12035N-Acetyl-L-CysteineHCID 682631,1'-CarbonyldiimidazoleHCID 758094-Bromobutyric acidHCID 2723922Sodium ethoxide

Product 1

HCID 57291887HCID 57291887, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-bromobutyric acid (5.1 g, 30.6 mmoles) and 1,1′-carbonyldiimidazol (5.61 g, 34.6 mmoles)) in chloroform (50 ml) is left at room temperature under stirring for 1 hour. To the reaction mixture N-acetyl cysteine (5 g, 30.6 mmoles) dissolved in N,N-dimethylformamide (5 ml) and sodium ethylate (50 mg) is added under stirring. After 24 hours the solution is washed with HCl 1% and brine, the organic phase is anhydrified with sodium sulphate and evaporated at reduced pressure. The obtained crude product is purified by chromatography on silica gel column, eluting with ethyl acetate/chloroform 7/3. N-acetyl-S-(4-bromobutyroyl) cysteine is obtained.

Workup

  1. stirringunder stirring
  2. washAfter 24 hours the solution is washed with HCl 1% and brine
  3. customevaporated at reduced pressure
  4. customThe obtained crude product
  5. customis purified by chromatography on silica gel column
  6. washeluting with ethyl acetate/chloroform 7/3

Sources & evidence

ORD record
ord-3f77f430f45d456ca00d6aea223a2153
Source dataset
uspto-grants-2007_03
Patent number
US07186708B2

Reaction notes

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