Tert-butoxycarbonylalanine → (S)-Methyl 3-bromo-1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate

HRID 524996

Reaction equation

HRID 524996 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].[C:12]([O:16][C:17]([NH:19][C@@H:20]([CH3:24])[C:21](O)=[O:22])=[O:18])([CH3:15])([CH3:14])[CH3:13]>>[Br:7][C:4]1[CH:5]=[CH:6][N:2]([NH:1][C:21](=[O:22])[C@@H:20]([NH:19][C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[CH3:24])[C:3]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

3

Reactant 2

HCID 85082Tert-butoxycarbonylalanineHCID 70979762methyl 1-amino-3-bromo-1H-pyrrole-2-carboxylate

Product 1

HCID 86722018(S)-Methyl 3-bromo-1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylateYield 61%

Procedure

The title compound was prepared following the experimental procedure described in preparation 20a from 6.1 g (18.38 mmol) of methyl 1-amino-3-bromo-1H-pyrrole-2-carboxylate and 3.5 g (28.50 mmol) of (S)-2-(tert-butoxycarbonylamino)propanoic acid (purchased from Aldrich). The crude product was purified by flash chromatography in hexane/ethyl acetate (0 to 25%) to afford 4.34 g (61% 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 (0 to 25%)

Sources & evidence

ORD record
ord-9ef3d73f5e0747bea670c900ac9d61e2
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Linked notes

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