N-Acetyl-L-Cysteine → HCID 178418393, compound

HRID 583534Notes

Reaction equation

HRID 583534 reaction equation
[CH3:1][CH:2]([CH2:17][CH3:18])[CH:3]([N:7]1[C:11](=[O:12])[C:10]2[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=2[S:8]1)[C:4]([OH:6])=[O:5].C(N[C@H:23]([C:26]([OH:28])=[O:27])[CH2:24][SH:25])(=O)C>CO>[C:11]([NH:7][SH:25]([CH2:24][CH2:23][C:26]([OH:28])=[O:27])[S:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[C:11]([NH:7][CH:3]([CH:2]([CH3:1])[CH2:17][CH3:18])[C:4]([OH:6])=[O:5])=[O:12])(=[O:12])[CH3:10]

Participants

4

Reactant 2

HCID 12035N-Acetyl-L-CysteineHCID 178926623-Methyl-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)pentanoic acid

Product 1

HCID 178418393HCID 178418393, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.58 g (2.2 mmol) of [S-(R*,R*)]-3-methyl-2-(3-oxo-3H-benzo[d]isothiazol-2-yl)pentanoic acid in 20 mL of methanol was treated with 0.36 g (2.2 mmol) of N-acetyl-L-cysteine and the reaction was stirred at room temperature for 18 hours. The solvent was removed in vacuo and the residue was triturated with 100 mL of 60° C. water. The water was decanted and the solid was dissolved in 50 mL of ethyl acetate. The organic solution was dried (MgSO4), filtered and evaporated in vacuo to give the title compound as a white, solid foam, mp 85-90° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was triturated with 100 mL of 60° C. water
  3. customThe water was decanted
  4. dissolutionthe solid was dissolved in 50 mL of ethyl acetate
  5. dry with materialThe organic solution was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-13b0d340533f4bedb58c5f5822d33a6d
Source dataset
uspto-grants-1999_07
Patent number
US05929114

Reaction notes

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