Acetic Acid → HCID 86757828, compound

HRID 275861Notes

Reaction equation

HRID 275861 reaction equation
N[C:2]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[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.C(OC1C=CC(C=O)=CC=1)C1C=CC=CC=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[C:16]([O:15][C:13]([NH:12][CH2:11][C:7]1[CH:6]=[C:5]([CH:4]([OH:20])[C:3]2[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][CH:2]=2)[CH:10]=[CH:9][CH:8]=1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 5003444Sodium cyanoborohydrideHCID 54566062HCID 54566062, compound

Product 1

HCID 86757828HCID 86757828, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

In methanol (6 ml) were dissolved 2-amino-α-(3-tert-butoxycarbonylaminomethylphenyl)-5-methyloxybenzyl alcohol (0.18 g), 4-benzyloxy-benzaldehyde (0.12 g) and acetic acid (0.02 g). To the solution was added sodium cyano borohydride (0.02 mg). The mixture was stirred for 30 minutes at 60° C. The reaction mixture was concentrated, to which were added ethyl acetate (30 ml) and water (50 ml). The mixture was shaken. 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-(4-benzyloxybenzyl)-α-(3-tert-butoxycarbonylaminomethylphenyl-5-methyloxybenzyl alcohol as a colorless crystalline product (0.17 g). m.p.:86-87° C.

Workup

  1. concentrationThe reaction mixture was concentrated, to which
  2. additionwere added ethyl acetate (30 ml) and water (50 ml)
  3. stirringThe mixture was shaken
  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-6ce62d59793548aa9159795263862f1d
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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