Acetic Acid → a-(3-Tert-butoxycarbonylaminomethylphenyl)-5-chloro-2-[(3-phenyl)-2-propenyl]amino-benzyl alcohol

HRID 275872Notes

Reaction equation

HRID 275872 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)[CH:27]=[CH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(O)(=O)C.[BH4-].C([Na])#N>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]([Cl:25])[CH:23]=[CH:24][C:2]=2[NH:1][CH2:26][CH:27]=[CH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:10]=[CH:9][CH:8]=1)=[O:14])([CH3:18])([CH3:19])[CH3:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3073-Phenylprop-2-EnalHCID 543588652-Amino-5-chloro-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcoholHCID 178511851HCID 178511851, compound

Product 1

HCID 54038371a-(3-Tert-butoxycarbonylaminomethylphenyl)-5-chloro-2-[(3-phenyl)-2-propenyl]amino-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 (0.6 g) produced in Example (1) and cinnamaldehyde.(0.5 g). To the solution was added acetic acid (0.11 g). To the mixture was added, while stirring at room temperature, cyano sodium borohydride (0.12 g). The reaction mixture was stirred for 40 minutes at 60° C., which was concentrated. The concentrate was subjected to extraction by the addition of water (30 ml) and ethyl acetate (50 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 a-(3-tert-butoxycarbonylaminomethylphenyl)-5-chloro-2-[(3-phenyl)-2-propenyl]amino-benzyl alcohol (0.8 g) as a colorless oily product.

Workup

  1. additionTo the mixture was added
  2. stirringThe reaction mixture was stirred for 40 minutes at 60° C.
  3. concentrationwhich was concentrated
  4. extractionThe concentrate was subjected to extraction by the addition of water (30 ml) and ethyl acetate (50 ml)
  5. washThe organic layer was washed 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-51f220a8d14a4fdcba5bdfe5cfafbddc
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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