(S)-phenylmethyl-[1-methyl-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate → (S)-2-Amino-N-1H-pyrrol-1-ylpropanamide

HRID 22381Notes

Reaction equation

HRID 22381 reaction equation
C1(COC(=O)[NH:10][C@@H:11]([CH3:20])[C:12](=[O:19])[NH:13][N:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)C=CC=CC=1>[Pd].CO>[NH2:10][C@@H:11]([CH3:20])[C:12]([NH:13][N:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1)=[O:19]

Participants

4

Reactant 1

HCID 15838188(S)-phenylmethyl-[1-methyl-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate

Product 1

HCID 53648891(S)-2-Amino-N-1H-pyrrol-1-ylpropanamideYield 89.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The CBZ group of (S)-phenylmethyl-[1-methyl-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate (5.50 g) was cleaved in a minimal volume of methanol over 5% Pd-C (0.83 g) with H2 (g) (468 ml) under atmospheric conditions. The catalyst was removed by filtration through a pad of celite and the filter cake was washed with methanol. The combined filtrate was concentrated and the residue purified via flash column chromatography (silica gel, 20% EtOH/ethyl acetate) to afford 2.62 g of the desired product as an oil which crystallized on standing, m.p. 81°-82° C.

Workup

  1. customThe catalyst was removed by filtration through a pad of celite
  2. washthe filter cake was washed with methanol
  3. concentrationThe combined filtrate was concentrated
  4. customthe residue purified via flash column chromatography (silica gel, 20% EtOH/ethyl acetate)

Sources & evidence

ORD record
ord-eb350459b0d14ffb9ffefad46ef72e54
Source dataset
uspto-grants-1995_06
Patent number
US05428053

Reaction notes

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