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

HRID 1868650Notes

Reaction equation

HRID 1868650 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15]([NH:17][CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])=[O:16])=[C:5]2[OH:26]>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15]([NH:17][CH2:18][C:19]([OH:21])=[O:20])=[O:16])=[C:5]2[OH:26]

Participants

3

Reactant 1

HCID 670994061,1-Dimethylethyl N-((6-fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate

Product 1

HCID 54748140N-((6-Fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycineYield 74.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1,1-dimethylethyl N-((6-fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (0.6 g, 2 mmol) in 3 mL TFA was stirred at room temperature for 30 minutes. The mixture was concentrated and triturated in ether 20 mL. The solid was filtered, washed with 10 mL ether, and dried under high vacuum to give 0.46 g of the product as an off-white solid. MS m/e=308 (M+H)+. Calculated for C15H14FNO5 307.09.

Workup

  1. concentrationThe mixture was concentrated
  2. customtriturated in ether 20 mL
  3. filtrationThe solid was filtered
  4. washwashed with 10 mL ether
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-f384affce18249d99a0a21b2f65d5b71
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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