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

HRID 327825Notes

Reaction equation

HRID 327825 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 131718294(R)-phenylmethyl-[1-methyl-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate

Product 1

HCID 53648892(R)-2-Amino-N-1H-pyrrol-1-ylpropanamideYield 77.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The CBZ group of (R)-phenylmethyl-[1-methyl-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate (5.13 g) was cleaved in a minimal volume of methanol over 5% Pd-C (1.03 g) with H2 (g) (436 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 filtrates were concentrated and the residue purified via flash column chromatography (silica gel, 30% EtOH/EtOAc), affording 2.11 g of the product as a oil which crystallized on standing, m.p. 63°-66° 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 filtrates were concentrated
  4. customthe residue purified via flash column chromatography (silica gel, 30% EtOH/EtOAc)

Sources & evidence

ORD record
ord-43e3a37f742648ef86e5b2d466d68fef
Source dataset
uspto-grants-1993_12
Patent number
US05274116

Reaction notes

Loading…