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

HRID 275830Notes

Reaction equation

HRID 275830 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.[CH:26](=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.C(OCC)(=O)C>[CH2:26]([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:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 543588652-Amino-5-chloro-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol

Product 1

HCID 543305022-Benzylamino-5-chloro-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcoholYield 104.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-amino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.7 g) in methanol (7 ml) were added benzaldehyde (229 mg) and acetic acid (130 mg). The mixture was stirred for 10 minutes at room temperature, to which was added sodium cyano-borohydride (135 mg). The mixture was stirred for 30 minutes at room temperature, to which was added ethyl acetate ester (50 ml). The mixture was washed with water and dried over anhydrous MgSO4, followed by distilling off the solvent. The residue was purified by means of a silica gel column chromatography to give the object 2-benzylamino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.91 g) as a colorless oily compound.

Workup

  1. stirringThe mixture was stirred for 30 minutes at room temperature, to which
  2. washThe mixture was washed with water
  3. dry with materialdried over anhydrous MgSO4
  4. distillationby distilling off the solvent
  5. customThe residue was purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-cc174cc5bda541d0b8a8c96e27106f66
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

Loading…