Trifluoroacetic acid → N-((5-Chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycine

HRID 2078245Notes

Reaction equation

HRID 2078245 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([OH:26])=[C:5]([C:15]([NH:17][CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])=[O:16])[C:6](=[O:14])[C:7]2([CH3:13])[CH3:12].C(O)(C(F)(F)F)=O>O>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([OH:26])=[C:5]([C:15]([NH:17][CH2:18][C:19]([OH:21])=[O:20])=[O:16])[C:6](=[O:14])[C:7]2([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86629259tert-Butyl N-((5-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate

Product 1

HCID 57983417N-((5-Chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycineYield 97.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

tert-Butyl N-((5-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (204 mg, 537 μmol) was stirred in TFA (2 mL, 26924 μmol) for 25 minutes. Water was added. The resulting precipitate was filtered and washed with water to give a white solid (169 mg). MS m/e=324 (M+H)+. Calculated for C15H14ClNO5 323.06.

Workup

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

Sources & evidence

ORD record
ord-e108a4db71ca42aea27a84ac766dc6ad
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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