Trifluoroacetic acid → HCID 57983512, compound

HRID 2078161Notes

Reaction equation

HRID 2078161 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([OH:27])=[C:8]([C:16]([NH:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])=[O:17])[C:9](=[O:15])[C:10]2([CH3:14])[CH3:13])=[CH:5][CH:4]=1.C(O)(C(F)(F)F)=O>>[F:1][C:2]([F:28])([F:29])[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([OH:27])=[C:8]([C:16]([NH:18][CH2:19][C:20]([OH:22])=[O:21])=[O:17])[C:9](=[O:15])[C:10]2([CH3:14])[CH3:13])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67100084HCID 67100084, compound

Product 1

HCID 57983512HCID 57983512, compoundYield 30.5%

Procedure

1,1-Dimethylethyl N-((7-trifluoromethyl-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (380 mg, 919 μmol) was stirred in TFA (2 mL, 26924 μmol) at room temperature for 30 minutes. The reaction mixture was partitioned between water and EtOAc. The organic layer was separated, dried (MgSO4), and concentrated in vacuo to give a yellow solid. The solid was then washed with water, ether, and EtOAc to give the desired product as an off-white solid (100 mg). MS (m/e)=358.1 (M+H)+. Calculated for C16H14F3NO5 357.08.

Workup

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give a yellow solid
  6. washThe solid was then washed with water, ether, and EtOAc

Sources & evidence

ORD record
ord-87b08ee7b4c145468fa4b76f60bad7d5
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

Loading…