benzyloxycarbonyl-L-valyl-L-proline t-butyl ester → Z-Val-pro-OH

HRID 1636967Notes

Reaction equation

HRID 1636967 reaction equation
C([O:5][C:6](=[O:29])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:28])[C@H:13]([CH:25]([CH3:27])[CH3:26])[NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])(C)(C)C>CO.[Pd]>[CH2:18]([O:17][C:15]([NH:14][C@H:13]([C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:29])=[O:5])=[O:28])[CH:25]([CH3:27])[CH3:26])=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 1

HCID 10549214benzyloxycarbonyl-L-valyl-L-proline t-butyl ester

Product 1

HCID 10783923Z-Val-pro-OHYield 69.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-benzyloxycarbonyl-L-valyl-L-proline tert-butyl ester (20 g) in methanol (300 ml) was hydrogenated at 50 psi over 10% palladium on carbon catalyst (2 g) for 12 hours. The reaction mixture was then filtered through diatomaceous earth and the filter cake washed with methanol. The filtrate was evaporated to give L-valyl-L-proline tert-butyl ester (A) (12 g) as an oil; NMR (300 MHz, d6 -DMSO): 0.80(d,3H), 0.92(d,3H), 1.74(s,9H), 1.79-2.15(m,5H), 3.22(d,1H), 3.30(bs,2H), 3.40(m,1H), 3.62(m,1H), 4.16(dd,1H).

Workup

  1. filtrationThe reaction mixture was then filtered through diatomaceous earth
  2. washthe filter cake washed with methanol
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-77e679da0aa04ce3b3d7dd0ef66962ae
Source dataset
uspto-grants-2000_03
Patent number
US06037363

Reaction notes

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