N-Ethoxycarbonylmethyl-N-tert.-butoxycarbonyl-2-(R)-amino-3-(4-methoxyphenyl)-propionic acid benzyl ester → n-Ethoxycarbonylmethyl-n-tert-butoxycarbonyl-2-(r)-amino-3-(4-methoxyphenyl)-propionic acid

HRID 1279103Notes

Reaction equation

HRID 1279103 reaction equation
C([O:8][C:9](=[O:34])[C@H:10]([N:20]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)C1C=CC=CC=1>CO.[Pd]>[CH2:32]([O:31][C:29]([CH2:28][N:20]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[C@H:10]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[C:9]([OH:34])=[O:8])=[O:30])[CH3:33]

Participants

4

Reactant 1

HCID 57276308N-Ethoxycarbonylmethyl-N-tert.-butoxycarbonyl-2-(R)-amino-3-(4-methoxyphenyl)-propionic acid benzyl ester

Product 1

HCID 22958574n-Ethoxycarbonylmethyl-n-tert-butoxycarbonyl-2-(r)-amino-3-(4-methoxyphenyl)-propionic acidYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-Ethoxycarbonylmethyl-N-tert.-butoxycarbonyl-2-(R)-amino-3-(4-methoxyphenyl)-propionic acid benzyl ester (1.50 g) were dissolved in 40 mL of methanol and hydrogenated for 4 h at room temperature using 0.3 g palladium on charcoal (10%) as catalyst. Filtration followed by concentration in vacuo affords 1.05 g (87%) of the title compound as a colorless oil. (−)-APCI-MS: 381 ([M−H]−).

Workup

  1. filtrationFiltration
  2. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-e0c4a31aad8145a589e21d8342d11825
Source dataset
uspto-grants-2002_09
Patent number
US06444672B1

Reaction notes

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