Methyl 4-Formylbenzoate → HCID 68773281, compound

HRID 1711198Notes

Reaction equation

HRID 1711198 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][C@@H:8]([CH2:28][NH2:29])[CH2:9][O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[CH:31]([C:33]1[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=1)=O.[BH4-].[Na+]>CO.[NH4+].[Cl-]>[CH3:40][O:39][C:37](=[O:38])[C:36]1[CH:41]=[CH:42][C:33]([CH2:31][NH:29][CH2:28][C@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:30])[CH2:9][O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:34][CH:35]=1

Participants

6

Reactant 3

HCID 15294Methyl 4-FormylbenzoateHCID 4311764Sodium borohydrideHCID 68774675HCID 68774675, compound

Product 1

HCID 68773281HCID 68773281, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 25517Ammonium ChlorideCatalystHCID 887MethanolSolvent

Procedure

[(S)-1-Aminomethyl-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-carbamic acid tert-butyl ester (640 mg, 1.44 mmol) was stirred with methyl 4-formylbenzoate (237 mg, 1.44 mmol) in CH3OH (3 ml) at rt for 2 h. NaBH4 (58 mg, 1.44 mmol) was added. The mixture was stirred at rt for 20 min. Several drops of saturated aqueous NH4Cl were added. The mixture was then partitioned between CH2Cl2 and water (20 ml/20 ml). The organic layer was concentrated to give 4-{[(S)-2-tert-butoxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-propylamino]-methyl}-benzoic acid methyl ester (650 mg, 76%).

Workup

  1. customThe mixture was then partitioned between CH2Cl2 and water (20 ml/20 ml)
  2. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-b8d901c87b6c4707850198f9117aa842
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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