HCID 67099310, compound → N-((6-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycine

HRID 2078129Notes

Reaction equation

HRID 2078129 reaction equation
[Br: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>[Br: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 67099310HCID 67099310, compound

Product 1

HCID 57983339N-((6-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycineYield 50%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1,1-dimethylethyl N-((6-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (145 mg, 342 μmol) in TFA (2 mL) was stirred at 23° C. After 30 minutes, the reaction was concentrated in vacuo, and diluted with water (25 mL). A white solid precipitated which was collected by filtration, washed with diethyl ether (5 mL), and dried under vacuum, affording 63 mg of N-((6-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycine. MS m/e=366.0 (M−H)−. Calculated for C15H14BrNO5 367.01.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. additiondiluted with water (25 mL)
  3. customA white solid precipitated which
  4. filtrationwas collected by filtration
  5. washwashed with diethyl ether (5 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-87df5c60f7bd4f1ca839b72c30071631
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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