N-carbobenzyloxyalanine → (S)-Methyl 1-(2-(benzyloxycarbonylamino)propanamido)-3-Bromo-1H-Pyrrole-2-carboxylate

HRID 525030

Reaction equation

[NH2:1][N:2]1[CH:6]=[CH:5][C:4]([Br:7])=[C:3]1[C:8]([O:10][CH3:11])=[O:9].[CH2:12]([O:19][C:20]([NH:22][C@@H:23]([CH3:27])[C:24](O)=[O:25])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([O:19][C:20]([NH:22][C@@H:23]([CH3:27])[C:24]([NH:1][N:2]1[CH:6]=[CH:5][C:4]([Br:7])=[C:3]1[C:8]([O:10][CH3:11])=[O:9])=[O:25])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Reactant 2

HCID 736104N-carbobenzyloxyalanine

HCID 70979762methyl 1-amino-3-bromo-1H-pyrrole-2-carboxylate

Product 1

HCID 86722049(S)-Methyl 1-(2-(benzyloxycarbonylamino)propanamido)-3-Bromo-1H-Pyrrole-2-carboxylateYield 89.6%

Procedure

The title compound was prepared from methyl 1-amino-3-bromo-1H-pyrrole-2-carboxylate (9.05 g, 25.6 mmol) and (S)-2-(benzyloxycarbonylamino)propanoic acid (5.72 g, 25.6 mmol) following the experimental procedure described in Preparation 73a. 9.73 g (84% yield) of the desired compound were obtained.

Sources & evidence

ORD record: ord-b2e06ac5adc74ca9a1c9c1efe94f92a2
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340547B2

Linked notes

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