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

HRID 1868738Notes

Reaction equation

HRID 1868738 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-def49429772e468dbb8aff91174c2e28
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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