HCID 67100102, compound → HCID 57983555, compound

HRID 2078181Notes

Reaction equation

HRID 2078181 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-ad2c2a238e83430fabea0c572c804618
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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