HCID 67099645, compound → HCID 54746529, compound

HRID 1868635Notes

Reaction equation

HRID 1868635 reaction equation
[OH:1][C:2]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([F:20])([F:19])[F:18])[CH:15]=2)[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[C:4](=[O:21])[C:3]=1[C:22]([NH:24][CH2:25][C:26]([O:28]C(C)(C)C)=[O:27])=[O:23]>C(O)(C(F)(F)F)=O>[OH:1][C:2]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([F:18])([F:20])[F:19])[CH:15]=2)[C:5]2([CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[C:4](=[O:21])[C:3]=1[C:22]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:23]

Participants

3

Reactant 1

HCID 67099645HCID 67099645, compound

Product 1

HCID 54746529HCID 54746529, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1,1-dimethylethyl N-((4-hydroxy-2-oxo-6-(trifluoromethyl)-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-yl)carbonyl)glycinate (500 mg, 1098 μmol) in TFA (4 mL) was stirred at 23° C. After 25 minutes, the reaction was concentrated in vacuo and azeotroped with DCM (2×10 mL). The crude solid was washed with diethyl ether affording 356 mg of N-((4-hydroxy-2-oxo-6-(trifluoromethyl)-2′,3′,5′,6′-tetrahydro-2H-spiro[naphthalene-1,4′-pyran]-3-yl)carbonyl)glycine. MS m/e=400.1 (M+H)+. Calculated for C18H16F3NO6 399.09.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customazeotroped with DCM (2×10 mL)
  3. washThe crude solid was washed with diethyl ether affording 356 mg of N-((4-hydroxy-2-oxo-6-(trifluoromethyl)-2′,3′,5′,6′-tetrahydro-2H-spiro[naphthalene-1,4′-pyran]-3-yl)carbonyl)glycine

Sources & evidence

ORD record
ord-35da1cbd59744eb584d1cf2e4e75290e
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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