S-(o-Nitrophenyl)-N-acetyl-D-cysteine → S-(o-Nitrophenyl)-D-cysteine

HRID 53119Notes

Reaction equation

HRID 53119 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH2:11][C@H:12]([C:17]([OH:19])=[O:18])[NH:13]C(=O)C)([O-:3])=[O:2]>S(=O)(=O)(O)O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH2:11][C@H:12]([C:17]([OH:19])=[O:18])[NH2:13])([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 13375098S-(o-Nitrophenyl)-N-acetyl-D-cysteine

Product 1

HCID 13375100S-(o-Nitrophenyl)-D-cysteineYield 100%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 13.6 g (47.9 mmol) of S-(o-nitrophenyl)-N-acetyl-D-cysteine was refluxed in 57 mL of 18M sulfuric acid (H2SO4) for 1 hour. The bright yellow solution was cooled to 0° C. and concentrated. Ammonium hydroxide (NH4OH) was added to adjust the pH=5.4. The resulting precipitate was filtered and dried to yield 11.6 g (100% ) of product.

Workup

  1. concentrationconcentrated
  2. additionAmmonium hydroxide (NH4OH) was added
  3. filtrationThe resulting precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-b7167f9134904423ae762dc2aecb6d72
Source dataset
uspto-grants-1997_04
Patent number
US05618808

Reaction notes

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