1,1-Dimethylethyl N-((4-hydroxy-1,1-dimethyl-2-oxo-5-(trifluoromethyl)-naphthalen-3-yl)carbonyl)glycinate → N-((4-Hydroxy-1,1-dimethyl-2-oxo-5-(trifluoromethyl)-naphthalen-3-yl)carbonyl)glycine

HRID 2078102Notes

Reaction equation

HRID 2078102 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:12]([F:15])([F:14])[F:13])[C:5]([CH3:17])([CH3:16])[C:4](=[O:18])[C:3]=1[C:19]([NH:21][CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])=[O:20]>C(O)(C(F)(F)F)=O>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:12]([F:14])([F:15])[F:13])[C:5]([CH3:17])([CH3:16])[C:4](=[O:18])[C:3]=1[C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20]

Participants

3

Reactant 1

HCID 670997161,1-Dimethylethyl N-((4-hydroxy-1,1-dimethyl-2-oxo-5-(trifluoromethyl)-naphthalen-3-yl)carbonyl)glycinate

Product 1

HCID 57983468N-((4-Hydroxy-1,1-dimethyl-2-oxo-5-(trifluoromethyl)-naphthalen-3-yl)carbonyl)glycineYield 6.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1,1-Dimethylethyl N-((4-hydroxy-1,1-dimethyl-2-oxo-5-(trifluoromethyl)-naphthalen-3-yl)carbonyl)glycinate (30 mg, 73 μmol) was stirred in TFA (5 mL) for 15 minutes. The TFA was then removed under vacuum. The residue was purified by preparatory scale TLC (5% MeOH/DCM eluent) to give the desired product as a light yellow oil (1.6 mg). MS (m/z)=358.4 (M+H)+. Calculated for C16H14F3NO5 357.08.

Workup

  1. customThe TFA was then removed under vacuum
  2. customThe residue was purified by preparatory scale TLC (5% MeOH/DCM eluent)

Sources & evidence

ORD record
ord-b7337dfb814a476c8bc89eb51401c751
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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