Trifluoroacetic acid → N-((7-Phenyl-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycine

HRID 1868759Notes

Reaction equation

HRID 1868759 reaction equation
[C:1]1([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:31])=[C:12]([C:20]([NH:22][CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])=[O:21])[C:13](=[O:19])[C:14]3([CH3:18])[CH3:17])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>>[C:1]1([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([OH:31])=[C:12]([C:20]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21])[C:13](=[O:19])[C:14]3([CH3:17])[CH3:18])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 671000071,1-Dimethylethyl N-((7-phenyl-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate

Product 1

HCID 57983357N-((7-Phenyl-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycineYield 95.6%

Procedure

1,1-Dimethylethyl N-((7-phenyl-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (169 mg, 401 μmol) was stirred in TFA (1 mL, 13462 μmol) at room temperature for 20 minutes. The reaction mixture was partitioned between water and EtOAc. The organic layer was separated, dried (MgSO4), and concentrated in vacuo to give the desired product as a yellow solid (140 mg). MS (m/z)=366.2 (M+H)+. Calculated for C21H19NO5 365.13.

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

Sources & evidence

ORD record
ord-8d514e8cf1bd4ffda0912c038ac41ca2
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

Loading…