3-benzyloxy-2-[N-(tert-butoxycarbonyl)amino]-2-methylpropanoic acid tert-butyl ester → 2-[N-(tert-butoxycarbonyl)amino]-3-hydroxy-2-methylpropanoic acid tert-butyl ester

HRID 1669924Notes

Reaction equation

HRID 1669924 reaction equation
[C:1]([O:5][C:6](=[O:26])[C:7]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([CH3:17])[CH2:8][O:9]CC1C=CC=CC=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:26])[C:7]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([CH3:17])[CH2:8][OH:9])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 109813793-benzyloxy-2-[N-(tert-butoxycarbonyl)amino]-2-methylpropanoic acid tert-butyl ester

Product 1

HCID 111193112-[N-(tert-butoxycarbonyl)amino]-3-hydroxy-2-methylpropanoic acid tert-butyl esterYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of the benzyl ether 8 (540 mg, 1.48 mmol) and 10% Pd—C (130 mg) in 20 mL of CH3OH was stirred under an H2 atmosphere overnight. The reaction mixture was filtered over Celite?, and the filtrate was concentrated under reduced pressure. Purification via silica gel column chromatography (30% EtOAc in hexane) provided a quantitative yield of 9 (407 mg, 100%) as a colorless solid: mp 44-45° C. (EtOAc/hexane); 1H NMR (CDCl3) 6.437 (3H, s), 1.442 (9H, s), 1.48 (9H, s), 3.72 (1H, d, J=11.2), 4.00 (1H, d, J=11.2), 5.32 (1H, broad s). Anal. (C13H25NO5) C, H, N.

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. concentration, and the filtrate was concentrated under reduced pressure
  3. customPurification via silica gel column chromatography (30% EtOAc in hexane)

Sources & evidence

ORD record
ord-db283dbd4f454017a88b7cefb2ec95c5
Source dataset
uspto-grants-2011_08
Patent number
US07989649B2

Reaction notes

Loading…