{[2-{2-(S)-[Benzyloxy-carbonyl]-pyrrolidine-1-yl}-1-(R)-(4-methoxybenzyl)-2-oxo-ethyl]-tert.-butoxycarbonyl-amino}-acetic acid ethyl ester → {[2-{2(S)-Carboxy-pyrrolidin-1-yl}-1-(R)-(4-methoxybenzyl)-2-oxo-ethyl]-tert.-butoxycarbonyl-amino}-acetic acid ethyl ester

HRID 1008580Notes

Reaction equation

HRID 1008580 reaction equation
[CH2:1]([O:3][C:4](=[O:41])[CH2:5][N:6]([C@H:14]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)[C:15]([N:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[C:22]([O:24]CC1C=CC=CC=1)=[O:23])=[O:16])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:41])[CH2:5][N:6]([C@H:14]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)[C:15]([N:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[C:22]([OH:24])=[O:23])=[O:16])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH3:2]

Participants

4

Reactant 1

HCID 69780750{[2-{2-(S)-[Benzyloxy-carbonyl]-pyrrolidine-1-yl}-1-(R)-(4-methoxybenzyl)-2-oxo-ethyl]-tert.-butoxycarbonyl-amino}-acetic acid ethyl ester

Product 1

HCID 57033331{[2-{2(S)-Carboxy-pyrrolidin-1-yl}-1-(R)-(4-methoxybenzyl)-2-oxo-ethyl]-tert.-butoxycarbonyl-amino}-acetic acid ethyl esterYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.78 g of {[2-{2-(S)-[Benzyloxy-carbonyl]-pyrrolidin-1-yl}-1-(R)-(4-methoxybenzyl)-2-oxo-ethyl]-tert.-butoxycarbonyl-amino}-acetic acid ethyl ester were dissolved in 50 mL of methanol and hydrogenated for 3 h at room temperature using 0.4 g palladium on charcoal (10%) as catalyst. Filtration followed by concentration in vacuo affords 0.58 g (89%) of the title compound as a colorless oil. (−)-APCI-MS: 477 ([M−H]−).

Workup

  1. filtrationFiltration
  2. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-cfaf25963d9d458e81e05f1deb3c6d30
Source dataset
uspto-grants-2004_09
Patent number
US06797710B2

Reaction notes

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