Acetic Acid → 2-(4-Benzyloxybenzylamino)-alpha-(3-tert-butoxycarbonylaminomethylphenyl)-5-isobutyloxybenzyl alcohol

HRID 275841Notes

Reaction equation

HRID 275841 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[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.[CH2:30]([O:37][C:38]1[CH:45]=[CH:44][C:41]([CH:42]=O)=[CH:40][CH:39]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(O)(=O)C.[BH4-].C([Na])#N>CO.O>[CH2:30]([O:37][C:38]1[CH:39]=[CH:40][C:41]([CH2:42][NH:1][C:2]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:21][C:3]=2[CH:4]([OH:20])[C:5]2[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]=2)=[CH:44][CH:45]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 542166762-Amino-alpha-(3-tert-butoxycarbonylaminomethylphenyl)-5-isobutyloxybenzyl alcoholHCID 178511851HCID 178511851, compound

Product 1

HCID 544261852-(4-Benzyloxybenzylamino)-alpha-(3-tert-butoxycarbonylaminomethylphenyl)-5-isobutyloxybenzyl alcohol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

NMR(CDCl3) δ: 1.02(6H,d,J=6.6 Hz), 1.449(9H,s), 2.05(1H,m), 3.64(2H,d,J=6.6 Hz), 4.31(2H,d,J=5.6 Hz), 4.85(1H,m), 6.797(1H,s), 6.6-7.5(7H,m) (5) In methanol (12 ml) were dissolved 2-amino-α-(3-tert-butoxycarbonylaminomethylphenyl)-5-isobutyloxybenzyl alcohol (0.36 g), 4-benzyloxy-benzaldehyde (0.2 g) and acetic acid (0.05 g). To the solution was added cyano sodium borohydride (0.065 g). The mixture was stirred for 20 minutes at 60° C. To the reaction mixture was added water (6 ml), which was subjected to extraction with ethyl acetate (60 ml). The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off to leave 2-(4-benzyloxybenzylamino)-α-(3-tert-butoxycarbonylaminomethylphenyl)-5-isobutyloxybenzyl alcohol as a yellow oily product (0.45 g).

Workup

  1. extractionwas subjected to extraction with ethyl acetate (60 ml)
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-f68b9b5846e04b3cae980439a87d6d2d
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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