Trifluoroacetic acid → N-((7-Trifluoromethyl-4-hydroxy-2-oxo-2',3',5',6'-tetrahydro-spiro[naphthalene-1,4'-pyran]-3-yl)carbonyl)glycine

HRID 2078146Notes

Reaction equation

HRID 2078146 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:17]=[C:16]2[C:6]([C:7]([OH:30])=[C:8]([C:19]([NH:21][CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])=[O:20])[C:9](=[O:18])[C:10]32[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)=[CH:5][CH:4]=1.C(O)(C(F)(F)F)=O>O>[F:32][C:2]([F:1])([F:31])[C:3]1[CH:17]=[C:16]2[C:6]([C:7]([OH:30])=[C:8]([C:19]([NH:21][CH2:22][C:23]([OH:25])=[O:24])=[O:20])[C:9](=[O:18])[C:10]32[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67099725HCID 67099725, compound

Product 1

HCID 57983367N-((7-Trifluoromethyl-4-hydroxy-2-oxo-2',3',5',6'-tetrahydro-spiro[naphthalene-1,4'-pyran]-3-yl)carbonyl)glycineYield 48.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,1-Dimethylethyl N-((7-trifluoromethyl-4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-yl)carbonyl)glycinate (1.29 g, 2.82 mmol) was stirred in TFA (3 mL, 40.4 mmol) at room temperature for 25 minutes. Water was added. The resulting precipitate was filtered and washed with water to give the desired product as a white solid (550 mg). MS (m/e)=400.1 (M+H)+. Calculated for C18H16F3NO6 399.09.

Workup

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

Sources & evidence

ORD record
ord-d985c07db71b4e449c2d35940c6c8720
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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