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

HRID 1052350Notes

Reaction equation

HRID 1052350 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)C=O>[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 dimethylformamide. 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 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-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. washwashed 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-dichloromethane)

Sources & evidence

ORD record
ord-e0c10eb6fed74eee9a9049bae35ee9d6
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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