Methanol → S-(o-aminophenyl)-N-carbobenzyloxy-D-cysteine

HRID 53121Notes

Reaction equation

HRID 53121 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:24]([OH:26])=[O:25])[NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])([O-])=O.CO.[Cl-].[NH4+]>[Zn]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH2:11][C@H:12]([C:24]([OH:26])=[O:25])[NH:13][C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 13375102S-(o-Nitrophenyl)-N-carbobenzyloxy-D-cysteine

Product 1

HCID 13375104S-(o-aminophenyl)-N-carbobenzyloxy-D-cysteineYield 84%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

To a yellow solution of 17.0 g (45.2 mmol) of S-(o-nitrophenyl)-N-carbobenzyloxy-D-cysteine in 800 mL of methanol containing 4.84 g (90.4 mmol) of ammonium chloride (NH4Cl) was added 41.1 g (633 mmol) of zinc dust. The resulting gray slurry was refluxed for 4 hours. The hot solution was then filtered, and the solid residue washed with an additional 200 mL of methanol. The filtrate was evaporated and the solid residue triturated with 320 mL of 1N HCl. Upon stirring for 1/2 hour, the initial gummy mass crystallized to a white solid. Filtration of the solid yielded 13.1 g (84%) of S-(o-aminophenyl)-N-carbobenzyloxy-D-cysteine.

Workup

  1. temperatureThe resulting gray slurry was refluxed for 4 hours
  2. filtrationThe hot solution was then filtered
  3. washthe solid residue washed with an additional 200 mL of methanol
  4. customThe filtrate was evaporated
  5. customthe solid residue triturated with 320 mL of 1N HCl
  6. customthe initial gummy mass crystallized to a white solid
  7. filtrationFiltration of the solid

Sources & evidence

ORD record
ord-ad40336019ad4769bb850d624a9d32bf
Source dataset
uspto-grants-1997_04
Patent number
US05618808

Reaction notes

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