O-Benzyl-N-(tert-butoxycarbonyl)-L-homoserine → (S)-tert-Butyl 4-(benzyloxy)-1-oxo-1-(2-(phenylcarbamoyl)-1H-pyrrol-1-ylamino)butan-2-ylcarbamate

HRID 525033Notes

Reaction equation

HRID 525033 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].[CH2:16]([O:23][CH2:24][CH2:25][C@H:26]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:27](O)=[O:28])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([O:23][CH2:24][CH2:25][C@H:26]([NH:30][C:31](=[O:32])[O:33][C:34]([CH3:36])([CH3:35])[CH3:37])[C:27](=[O:28])[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:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 15058464O-Benzyl-N-(tert-butoxycarbonyl)-L-homoserineHCID 709224541-amino-N-phenyl-1H-pyrrole-2-carboxamide

Product 1

HCID 86722052(S)-tert-Butyl 4-(benzyloxy)-1-oxo-1-(2-(phenylcarbamoyl)-1H-pyrrol-1-ylamino)butan-2-ylcarbamateYield 99.6%

Procedure

The title compound was prepared from 1-amino-N-phenyl-1H-pyrrole-2-carboxamide (0.65 g, 3.2 mmol) and (S)-4-(benzyloxy)-2-(tert-butoxycarbonylamino)butanoic acid (1.0 g, 3.2 mmol) following the experimental procedure described in Preparation 73a. 1.57 g (96% yield) of the desired compound were obtained.

Sources & evidence

ORD record
ord-46b1e72f7fd44e81986c33a8b9028987
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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