Acetic Acid → 2-(2-Benzyloxybenzylamino)-5-chloro-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol

HRID 275879

Reaction equation

HRID 275879 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:3]=1[CH:4]([OH:20])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]=1.[CH2:26]([O:33][C:34]1[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=1[CH:36]=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(O)(=O)C.[BH4-].C([Na])#N>CO>[CH2:26]([O:33][C:34]1[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=1[CH2:36][NH:1][C:2]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:3]=1[CH:4]([OH:20])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][NH:12][C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[CH:6]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3447842-(Benzyloxy)benzaldehydeHCID 543588652-Amino-5-chloro-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcoholHCID 178511851HCID 178511851, compound

Product 1

HCID 542535092-(2-Benzyloxybenzylamino)-5-chloro-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcoholYield 136.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

In methanol (20 ml) were dissolved 2-amino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.5 g) obtained in Example 1 (2) and 2-benzyloxybenzaldehyde (0.7 g). To the solution were added acetic acid (0.15 g) and cyano sodium borohydride (0.16 g). The mixture was stirred for 40 minutes at 60° C. The reaction mixture was concentrated, to which were added water (50 ml) and ethyl acetate (60 ml), followed by subjecting the mixture to extraction. The organic layer was separated, washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography to give 2-(2-benzyloxybenzylamino)-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (1.05 g) as a colorless oily product.

Workup

  1. concentrationThe reaction mixture was concentrated, to which
  2. additionwere added water (50 ml) and ethyl acetate (60 ml)
  3. extractionto extraction
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-e03e120bc9604b8b8cbd75e46166267b
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Linked notes

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