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

HRID 2078202Notes

Reaction equation

HRID 2078202 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:13])([CH3:12])[C:4](=[O:14])[C:3]=1[C:15]([NH:17][CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])=[O:16]>C(O)(C(F)(F)F)=O>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:13])([CH3:12])[C:4](=[O:14])[C:3]=1[C:15]([NH:17][CH2:18][C:19]([OH:21])=[O:20])=[O:16]

Participants

3

Reactant 1

HCID 670997981,1-Dimethylethyl N-((4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate

Product 1

HCID 57983511N-((4-Hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycineYield 95%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1,1-Dimethylethyl N-((4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (270 mg, 782 μmol) was dissolved in TFA (2 mL) at ambient temperature. The mixture was then stirred for 30 minutes. The reaction mixture was concentrated, suspended in hexanes, filtered, washed with hexanes, and dried in a vacuum oven to give the title compound (215 mg) as a white solid. MS (m/z)=290 (M+H)+. Calculated for C15H15NO5 289.1.

Workup

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

Sources & evidence

ORD record
ord-9d896d9907884784b0d33e56ae67deab
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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