HCID 67100102, compound → HCID 57983555, compound

HRID 1868773Notes

Reaction equation

HRID 1868773 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[C:8]([CH3:14])([CH3:13])[C:7](=[O:15])[C:6]([C:16]([NH:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])=[O:17])=[C:5]2[OH:27]>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[C:8]([CH3:14])([CH3:13])[C:7](=[O:15])[C:6]([C:16]([NH:18][CH2:19][C:20]([OH:22])=[O:21])=[O:17])=[C:5]2[OH:27]

Participants

3

Reactant 1

HCID 67100102HCID 67100102, compound

Product 1

HCID 57983555HCID 57983555, compoundYield 112.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1,1-Dimethylethyl N-((6-chloro-8-fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-yl)carbonyl)glycinate (227 mg, 571 μmol) was dissolved in TFA (2 mL) and stirred at ambient temperature for 30 minutes. The resulting mixture was concentrated, precipitated with hexanes, filtered, washed with hexanes, and dried in a vacuum oven to give the title compound (219 mg, 112% yield) as a white solid. MS (m/z)=342 (M+H)+. Calculated for C15H13ClFNO5 341.05.

Workup

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

Sources & evidence

ORD record
ord-5f07788c8bee407e9d492bf0e776a691
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

Loading…