Methanol → HCID 54051866, compound

HRID 275847Notes

Reaction equation

HRID 275847 reaction equation
CO.[NH2:3][C:4]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:5]=1[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:9]=1)=[O:7].[BH4-].[Na+]>C(OC(=O)C)C>[NH2:3][C:4]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:5]=1[CH:6]([OH:7])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 183153632-Amino-3'-tert-butoxycarbonylamino-5-chlorobenzophenone

Product 1

HCID 54051866HCID 54051866, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a methanol (5 ml) solution of 2-amino-3′-tert-butoxycarbonylamino-5-chlorobenzophenone (0.4 g) was added sodium borohydride (66 mg). The mixture was stirred for one hour at room temperature, to which was added acetic acid ethyl ester (l00.ml). The mixture was washed with water and dried over anhydrous MgSO4. The solvent was then distilled off, and the residue was purified by means of a silica gel column chromatography to afford the object 2-amino-5-chloro-α-(3-tert-butoxycarbonylaminophenyl)benzyl alcohol (0.4 g) as a colorless oily product.

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried over anhydrous MgSO4
  3. distillationThe solvent was then distilled off
  4. customthe residue was purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-bd281731663c46b98dca129622651eb7
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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