Trifluoroacetic acid → N-((7-Bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)-L-alanine

HRID 2078163Notes

Reaction equation

HRID 2078163 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:27])=[C:7]([C:15]([NH:17][C@H:18]([C:20]([O:22]C(C)(C)C)=[O:21])[CH3:19])=[O:16])[C:8](=[O:14])[C:9]2([CH3:13])[CH3:12])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:27])=[C:7]([C:15]([NH:17][C@H:18]([C:20]([OH:22])=[O:21])[CH3:19])=[O:16])[C:8](=[O:14])[C:9]2([CH3:12])[CH3:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 670998931,1-Dimethylethyl N-((7-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)-L-alaninate

Product 1

HCID 57983473N-((7-Bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)-L-alanineYield 55.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,1-Dimethylethyl N-((7-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)-L-alaninate (184 mg, 436 μmol) was stirred in TFA (2 mL, 26924 μmol) at room temperature for 30 minutes. Water was added. The resulting precipitate was filtered and washed with water to give the desired product as a white solid (93 mg). MS (m/e)=382.1 (M+H)+. Calculated for C21H19NO5 381.02.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-0a47ff4544b4449a97d27ec94a6aed23
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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