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

HRID 1075719Notes

Reaction equation

HRID 1075719 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-a3c77f6425e14a268e1ed20804592028
Source dataset
uspto-grants-1999_05
Patent number
US05907043

Reaction notes

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