1,1-Dimethylethyl N-((6-phenyl-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate → N-((6-Phenyl-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycine

HRID 1868807Notes

Reaction equation

HRID 1868807 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[C:13]([CH3:18])([CH3:17])[C:12](=[O:19])[C:11]([C:20]([NH:22][CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])=[O:21])=[C:10]3[OH:31])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(C(F)(F)F)=O>[C:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[C:13]([CH3:18])([CH3:17])[C:12](=[O:19])[C:11]([C:20]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21])=[C:10]3[OH:31])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 670999281,1-Dimethylethyl N-((6-phenyl-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate

Product 1

HCID 57983521N-((6-Phenyl-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycineYield 34.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1,1-Dimethylethyl N-((6-phenyl-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (190 mg, 451 μmol) was dissolved in TFA (2 mL) at ambient temperature. The resulting mixture was then stirred for 30 minutes. The reaction mixture was concentrated, precipitated with ether, filtered, washed with ether, and dried in a vacuum oven to give the title compound (57 mg) as a white solid. MS (m/z)=366 (M+H)+. Calculated for C21H19NO5 365.13.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customprecipitated with ether
  3. filtrationfiltered
  4. washwashed with ether
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-9e8077463ce54e10963409175178b79f
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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