1,1-dimethylethyl N-((5-fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate → N-((5-Fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycine

HRID 1868833Notes

Reaction equation

HRID 1868833 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([OH:26])=[C:5]([C:15]([NH:17][CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])=[O:16])[C:6](=[O:14])[C:7]2([CH3:13])[CH3:12]>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([OH:26])=[C:5]([C:15]([NH:17][CH2:18][C:19]([OH:21])=[O:20])=[O:16])[C:6](=[O:14])[C:7]2([CH3:13])[CH3:12]

Participants

3

Reactant 1

HCID 670996891,1-dimethylethyl N-((5-fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate

Product 1

HCID 57983524N-((5-Fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1,1-Dimethylethyl N-((5-fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (116 mg, 319 μmol) was stirred in TFA (5 mL) for 15 minutes. The solvent was then removed in vacuo, and the residue was partitioned between DCM and water. The DCM layer was removed, and the solvent was removed in vacuo to give the product as a light yellow solid. MS m/e=308 (M+H)+. Calculated for C15H14FNO5 307.09.

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe residue was partitioned between DCM and water
  3. customThe DCM layer was removed
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4cb8e90a925e49bbb5dd1a7c0a7931fc
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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