Tert-butoxycarbonylalanine → (S)-tert-Butyl 1-(3-methyl-2-(phenylcarbamoyl)-1H-pyrrol-1-ylamino)-1-oxopropan-2-ylcarbamate

HRID 525000Notes

Reaction equation

HRID 525000 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][C:4]([CH3:7])=[C:3]1[C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9].[C:17]([O:21][C:22]([NH:24][C@@H:25]([CH3:29])[C:26](O)=[O:27])=[O:23])([CH3:20])([CH3:19])[CH3:18]>>[CH3:7][C:4]1[CH:5]=[CH:6][N:2]([NH:1][C:26](=[O:27])[C@@H:25]([NH:24][C:22](=[O:23])[O:21][C:17]([CH3:19])([CH3:18])[CH3:20])[CH3:29])[C:3]=1[C:8](=[O:9])[NH:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 85082Tert-butoxycarbonylalanineHCID 709224391-amino-3-methyl-N-phenyl-1H-pyrrole-2-carboxamide

Product 1

HCID 90200400(S)-tert-Butyl 1-(3-methyl-2-(phenylcarbamoyl)-1H-pyrrol-1-ylamino)-1-oxopropan-2-ylcarbamateYield 23%

Procedure

Prepared from 2.00 g (9.29 mmol) of 1-amino-3-methyl-N-phenyl-1H-pyrrole-2-carboxamide and 2.11 g (11.15 mmol) of (S)-2-(tert-butoxycarbonylamino)propanoic acid following the experimental procedure described in Preparation 22a. After purification by flash chromatography (0 to 10% methanol in dichloromethane), 825 mg (23% yield) of the title product were obtained.

Workup

  1. customAfter purification by flash chromatography (0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-44934ff24ecd4ee2ab11fbbef7ec9a1a
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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