N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl-L-proline phenylmethyl ester → Boc-ala-pro-OH

HRID 280795Notes

Reaction equation

HRID 280795 reaction equation
C([O:8][C:9](=[O:27])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:26])[C@H:16]([CH3:25])[NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])C1C=CC=CC=1.[H][H]>CO.[C].[Pd]>[C:21]([O:20][C:18]([NH:17][C@H:16]([C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9]([OH:27])=[O:8])=[O:26])[CH3:25])=[O:19])([CH3:22])([CH3:23])[CH3:24]

Participants

5

Reactant 2

HCID 13068139N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl-L-proline phenylmethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 11902919Boc-ala-pro-OHYield 92.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

N-t-butyloxycarbonyl-L-alanyl-L-proline benzyl ester (6.4 g, 17 m mole) was dissolved in methanol (100 ml). Hydrogen was passed for 3 hours through the solution in the presence of 10% palladium-carbon as a catalyst. The catalyst was removed by filtration and the solvent was distilled off under reduced pressure. The residue was crystallized in ethyl acetate-n-hexan to give N-t-butyloxycarbonyl-L-alanyl-L-proline (4.5 g, yield: 92.4%) having melting point of 155° to 157° C. and specific rotatory power [α]D25 =-90.5° (C=1, ethanol). The product gave a single spot on thin layer chromatography.

Workup

  1. customThe catalyst was removed by filtration
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was crystallized in ethyl acetate-n-hexan

Sources & evidence

ORD record
ord-d603378aca3648c8988eb8feb9d72c9f
Source dataset
uspto-grants-1986_05
Patent number
US04590178

Reaction notes

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