Trifluoroacetic acid → HCID 57983515, compound

HRID 1868799Notes

Reaction equation

HRID 1868799 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[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](=[CH:10][C:11]=1[Cl:12])[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 2

HCID 6422Trifluoroacetic acidHCID 67099892HCID 67099892, compound

Product 1

HCID 57983515HCID 57983515, compoundYield 46.8%

Procedure

To 1,1-dimethylethyl N-((6,7-dichloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (235 mg, 567 μmol) was added TFA (2 mL) at ambient temperature. The mixture was stirred for 30 minutes and then concentrated, precipitated with ether, filtered, washed with ether, and dried in a vacuum oven to give the title compound (95 mg) as a white solid. MS (m/z)=358 (M+H)+. Calculated for C15H13Cl2NO5 357.02.

Workup

  1. concentrationconcentrated
  2. customprecipitated with ether
  3. filtrationfiltered
  4. washwashed with ether
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-c9a740e0e40d4c92a0993b1785bdc43a
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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