Tert-butoxycarbonylalanine → HCID 86722017, compound

HRID 524993Notes

Reaction equation

HRID 524993 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][C:4]([Br: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]>>[Br: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 70979311HCID 70979311, compound

Product 1

HCID 86722017HCID 86722017, compoundYield 51.4%

Procedure

The title compound was prepared following the experimental procedure described in preparation 20a from 810 mg (2.89 mmol) of 1-amino-3-bromo-N-phenyl-1H-pyrrole-2-carboxamide and 656 mg (3.47 mmol) of (S)-2-(tert-butoxycarbonylamino)propanoic acid (purchased from Aldrich). The crude product was purified by flash chromatography in hexane/ethyl acetate to afford 670 mg (49% yield) of the title compound.

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified by flash chromatography in hexane/ethyl acetate

Sources & evidence

ORD record
ord-3f219802bb1847c7a41a18b9cc3423a6
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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