Trifluoroacetic acid → N-((7-Chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycine

HRID 1868750Notes

Reaction equation

HRID 1868750 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:26])=[C:7]([C:15]([NH:17][CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])=[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>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:26])=[C:7]([C:15]([NH:17][CH2:18][C:19]([OH:21])=[O:20])=[O:16])[C:8](=[O:14])[C:9]2([CH3:13])[CH3:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 670999541,1-Dimethylethyl N-((7-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate

Product 1

HCID 57983346N-((7-Chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycineYield 66.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,1-Dimethylethyl N-((7-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (1.21 g, 3 mmol) was stirred in TFA (5 mL, 67 mmol) at room temperature for 20 minutes. Water was added. The resulting precipitate was filtered and washed with water to give the desired product as a white solid (650 mg). MS (m/e)=324.1 (M+H)+. Calculated for C15H14ClNO5 323.06.

Workup

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

Sources & evidence

ORD record
ord-88d0fd2aa0864ea381ffbc74e166c501
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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