Ammonium Chloride → O-(o-Aminophenyl)-N-t-butoxycarbonyl-D-serine

HRID 53125Notes

Reaction equation

HRID 53125 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][C@H:12]([C:21]([OH:23])=[O:22])[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([O-])=O.[Cl-].[NH4+]>CO.[Zn]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][C@H:12]([C:21]([OH:23])=[O:22])[NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 54196434N-Boc-O-(2-nitrophenyl)-D-serine

Product 1

HCID 53706577O-(o-Aminophenyl)-N-t-butoxycarbonyl-D-serineYield 100%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

A mixture of 8.98 g (0.0275M) of O-(o-nitrophenyl)-N-t-butoxycarbonyl-D-serine, 2.95 g (0.0551M) of ammonium chloride (NH4Cl) and 25 g (0.3856M) of zinc dust in 200 mL of methanol was stirred at room temperature for 18 hours. The solvent was evaporated and the residue dissolved in 200 mL of a 50/50 mixture of ethyl acetate and chloroform. The mixture was filtered and the filtrate evaporated to yield 8.15 g (100%) of product as an oil.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in 200 mL of a 50/50 mixture of ethyl acetate and chloroform
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-9ce3dc6381cc47299971c9336ed116a6
Source dataset
uspto-grants-1997_04
Patent number
US05618808

Reaction notes

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