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

HRID 275865Notes

Reaction equation

HRID 275865 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[BH4-].C([Na])#N.N[C:26]1[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][C:27]=1[CH:28]([OH:44])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:30]=1>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][C:26]1[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][C:27]=1[CH:28]([OH:44])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:30]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 743423-BenzyloxybenzaldehydeHCID 543588652-Amino-5-chloro-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcoholHCID 178511851HCID 178511851, compound

Product 1

HCID 544600152-(3-Benzyloxybenzyl)-5-chloro-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (15 ml) were dissolved 2-amino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol produced in Example 1-(2) (0.6 g) and 3-benzyloxybenzaldehyde (0.38 g). To the solution was added acetic acid (0.12 g). To the mixture was added dropwise, while stirring at room temperature, cyano sodium borohydride (0.13 g). The reaction mixture was stirred for one hour at 60° C., to which was then added water (50 ml), followed by extraction with ethyl acetate (80 ml). The organic layer was 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-(3-benzyloxybenzyl)-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.9 g) as a colorless oily product.

Workup

  1. additionTo the mixture was added dropwise
  2. stirringThe reaction mixture was stirred for one hour at 60° C., to which
  3. extractionadded water (50 ml), followed by extraction with ethyl acetate (80 ml)
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-7b16a1e94ea3450497e8cacd08744b99
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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