Tert-butoxycarbonylalanine → (S)-tert-Butyl 1-oxo-1-(2-(phenylcarbamoyl)-1H-pyrrol-1-ylamino)propan-2-ylcarbamate

HRID 524979Notes

Reaction equation

HRID 524979 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8].[C:16]([O:20][C:21]([NH:23][C@@H:24]([CH3:28])[C:25](O)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[O:26]=[C:25]([NH:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:8])[NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C@@H:24]([NH:23][C:21](=[O:22])[O:20][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:28]

Participants

5

Reactant 3

HCID 85082Tert-butoxycarbonylalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 709224541-amino-N-phenyl-1H-pyrrole-2-carboxamide

Product 1

HCID 70922144(S)-tert-Butyl 1-oxo-1-(2-(phenylcarbamoyl)-1H-pyrrol-1-ylamino)propan-2-ylcarbamateYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.00 g (9.94 mmol) of 1-amino-N-phenyl-1H-pyrrole-2-carboxamide were dissolved in 50 mL of DMF. To this solution, 2.07 g (10.94 mmol) of (S)-2-(tert-butoxycarbonylamino)propanoic acid (purchased from Aldrich®, cat. no. 13, 451-1) and 2.10 g (10.95 mmol) of EDC.HCl were added and the resulting reaction mixture was stirred at room temperature overnight. The solvent was then evaporated under vacuum, the residue was taken up in ethyl acetate and the organic solution was washed with an aqueous solution of sodium bicarbonate and brine, it was dried over magnesium sulphate, filtered and the solvent was evaporated. The product was purified by flash chromatography (0-5% methanol in dichloromethane). 2.21 g (60% yield) of the final product were obtained as a white solid.

Workup

  1. customthe resulting reaction mixture
  2. customThe solvent was then evaporated under vacuum
  3. washthe organic solution was washed with an aqueous solution of sodium bicarbonate and brine, it
  4. dry with materialwas dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe product was purified by flash chromatography (0-5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-0f6259f5a87d42e1b56b49d9fdd2d8de
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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