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

HRID 1598888Notes

Reaction equation

HRID 1598888 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-efbbd039f7dd4b7296752238a3aed013
Source dataset
uspto-grants-1998_04
Patent number
US05739157

Reaction notes

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