Trifluoroacetic acid → HCID 67099670, compound

HRID 1868725Notes

Reaction equation

HRID 1868725 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH3:14])([CH3:13])[C:8](=[O:15])[C:7]([C:16]([NH:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])=[O:17])=[C:6]2[OH:27])#[N:2].C(O)(C(F)(F)F)=O>O>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH3:14])([CH3:13])[C:8](=[O:15])[C:7]([C:16]([NH:18][CH2:19][C:20]([OH:22])=[O:21])=[O:17])=[C:6]2[OH:27])#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67099651HCID 67099651, compound

Product 1

HCID 67099670HCID 67099670, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,1-Dimethylethyl N-((6-cyano-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-yl)carbonyl)glycinate (124 mg, 335 μmol) was stirred in TFA (1 mL, 13462 μmol) at room temperature for 15 minutes. Water was added. The resulting precipitate was filtered. The green solid was dissolved in saturated NaHCO3 and washed with DCM. The aqueous layer was separated and acidified with 10% HCl. The resulting precipitate was filtered and washed with water to give the desired product as a white solid (41 mg). MS (m/e)=315.1 (M+H)+. Calculated for C16H14N2O5 314.09.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. dissolutionThe green solid was dissolved in saturated NaHCO3
  3. washwashed with DCM
  4. customThe aqueous layer was separated
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-73af7287e5ae48b9876cc321a98cfee0
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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