HCID 67099588, compound → HCID 54746530, compound

HRID 1868639Notes

Reaction equation

HRID 1868639 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[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]>C1(C)C=CC=CC=1>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:14])([F:15])[F:13])[CH:10]=2)[C:5]([CH3:16])([CH3:17])[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 67099588HCID 67099588, compound

Product 1

HCID 54746530HCID 54746530, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 1,1-dimethylethyl N-((4-hydroxy-1,1-dimethyl-2-oxo-6-(trifluoromethyl)-naphthalen-3-yl)carbonyl)glycinate (432 mg, 1045 μmol) in toluene (5 mL), was treated with silica gel (314 mg, 5225 μmol). The reaction was heated at 110° C. After 4 hours, the reaction was cooled to 23° C. and filtered. The residue was washed with DCM (150 mL), and the filtrates were discarded. The residue was subsequently washed with a 10% MeOH/DCM solution (1000 mL). The filtrate was concentrated in vacuo, affording 312 mg of the title compound. MS m/e=358.1 (M+H)+. Calculated for C16H14F3NO5 357.08.

Workup

  1. temperaturethe reaction was cooled to 23° C.
  2. filtrationfiltered
  3. washThe residue was washed with DCM (150 mL)
  4. washThe residue was subsequently washed with a 10% MeOH/DCM solution (1000 mL)
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d975d1f0810a4b359e786b7bcca4e3dc
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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