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

HRID 524998Notes

Reaction equation

HRID 524998 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][N: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>>[O:26]=[C:25]([NH:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7](=[O:8])[NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C@@H:24]([NH:23][C:21](=[O:22])[O:20][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:28]

Participants

4

Reactant 3

HCID 85082Tert-butoxycarbonylalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 211043521-Amino-N-phenyl-1H-imidazole-2-carboxamide

Product 1

HCID 86722020(S)-tert-Butyl 1-oxo-1-(2-(phenylcarbamoyl)-1H-imidazol-1-ylamino)propan-2-ylcarbamateYield 73%

Procedure

The title compound was prepared following the experimental procedure described in preparation 20a, from 1.12 g (5.54 mmol) of 1-amino-N-phenyl-1H-imidazole-2-carboxamide, 1.26 g (6.65 mmol) of (S)-2-(tert-butoxycarbonylamino)propanoic acid and 1.03 g (6.65 mmol) of EDC.HCl. The solid obtained was triturated in diisopropylether to give 1.51 g (67% yield) of the title compound.

Workup

  1. customThe title compound was prepared
  2. customThe solid obtained
  3. customwas triturated in diisopropylether

Sources & evidence

ORD record
ord-23d937da992b4672a5318439ccf0a56c
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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