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

HRID 1868757Notes

Reaction equation

HRID 1868757 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([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:2]=1.C(O)(C(F)(F)F)=O>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([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:2]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 671000221,1-Dimethylethyl N-((7-(3-pyridyl)-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate

Product 1

HCID 57983358N-((7-(3-Pyridyl)-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycineYield 59.5%

Procedure

1,1-Dimethylethyl N-((7-(3-pyridyl)-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (184 mg, 436 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, and the aqueous layer was extracted with EtOAc (2×). The combined organic layers were dried (MgSO4) and concentrated in vacuo to give the desired product as a yellow solid (95 mg). MS (m/e)=367.2 (M+H)+. Calculated for C21H19NO5 366.12.

Workup

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with EtOAc (2×)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-55475314e2304b4ab605eed81e6e6c67
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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