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

HRID 2418502Notes

Reaction equation

HRID 2418502 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 filtrate was distilled under reduced pressure leaving a residue. 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 filtrate was distilled under reduced pressure
  3. customleaving a residue
  4. customThe residue was crystallized in ethyl acetate-n-hexan

Sources & evidence

ORD record
ord-a3d6dad4667140afa6dee83b6a3da45b
Source dataset
uspto-grants-1984_09
Patent number
US04472381

Reaction notes

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