(S)-Phenylmethyl-[1-(hydroxymethyl)-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate → (S)-2-Amino-3-hydroxy-N-1H-pyrrol-1-ylpropanamide

HRID 1080454Notes

Reaction equation

HRID 1080454 reaction equation
C1(COC(=O)[NH:10][C@@H:11]([CH2:20][OH:21])[C:12](=[O:19])[NH:13][N:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)C=CC=CC=1>CO.[Pd]>[NH2:10][C@@H:11]([CH2:20][OH:21])[C:12]([NH:13][N:14]1[CH:15]=[CH:16][CH:17]=[CH:18]1)=[O:19]

Participants

4

Reactant 1

HCID 10979597(S)-Phenylmethyl-[1-(hydroxymethyl)-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate

Product 1

HCID 54410690(S)-2-Amino-3-hydroxy-N-1H-pyrrol-1-ylpropanamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-Phenylmethyl-[1-(hydroxymethyl)-2-oxo-2-(1H-pyrrol-1-ylamino)-ethyl]carbamate (4.90 g) was dissolved in 100 ml of methanol over 5% Pd/C (500 mg). The solution was hydrogenated at atmospheric pressure and room temperature until absorption of 80% of the theoretical amount of hydrogen. The catalyst was removed by filtration and the filtrate was evaporated to dryness. The residue was purified by flash column chromatography (silica gel, ethyl acetate/methanol 4:1) to afford the desired product as a powder. Recrystallization from ethyl acetate/methanol/hexane gave the product as needles (1.37 g), m.p. 135°-137° C.

Workup

  1. customThe solution was hydrogenated at atmospheric pressure and room temperature until absorption of 80% of the theoretical amount of hydrogen
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was purified by flash column chromatography (silica gel, ethyl acetate/methanol 4:1)

Sources & evidence

ORD record
ord-a5a2f8bcb42a4a64a266383725d275bc
Source dataset
uspto-grants-1996_12
Patent number
US05580987

Reaction notes

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