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

HRID 2078131Notes

Reaction equation

HRID 2078131 reaction equation
[C:1]([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)#[N:2].C(O)(C(F)(F)F)=O>O>[C:1]([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)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 670997611,1-Dimethylethyl N-((7-cyano-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-yl)carbonyl)glycinate

Product 1

HCID 67099886N-((7-Cyano-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycineYield 91.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,1-Dimethylethyl N-((7-cyano-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-yl)carbonyl)glycinate (163 mg, 440 μmol) was stirred in TFA (1 mL, 13462 μmol) at room temperature for 20 minutes. Water was added. The resulting precipitate was filtered and washed with water to give the desired product as an off-white solid (126 mg). MS (m/e)=315.1 (M+H)+. Calculated for C16H14N2O5 314.09.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-18500780bfa046c3b5254eaedc7e75e9
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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