HCID 14621631, compound → HCID 14621620, compound

HRID 1905360Notes

Reaction equation

HRID 1905360 reaction equation
[C:1]([N:9]([C:18]([C:20]1[C:29]2[C:24](=[C:25]([C:32]([F:35])([F:34])[F:33])[C:26]([O:30][CH3:31])=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)=[O:19])[CH2:10][C:11]([O:13]C(C)(C)C)=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O.O>[C:1]([N:9]([C:18]([C:20]1[C:29]2[C:24](=[C:25]([C:32]([F:33])([F:35])[F:34])[C:26]([O:30][CH3:31])=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)=[O:19])[CH2:10][C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 14621631HCID 14621631, compound

Product 1

HCID 14621620HCID 14621620, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-benzoyl-N-[[6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]glycine, 1,1-dimethylethyl ester (6.03 g, 12.4 mmole) in trifluoroacetic acid (40 mL) was stirred at room temperature for 10 minutes, then diluted with water (600 mL) and extracted with ether (2×300 mL). The extracts were combined, washed with saturated aqueous sodium chloride (1×100 mL), dried with magnesium sulfate, and the ether was removed. The resultant oil was suspended in water (300 mL) and the aqueous phase was slowly neutralized to pH 5 with 10% aqueous sodium hydroxide solution. The precipitate was collected by suction filtration, washed with water (2×25 mL), dried and flash chromatographed (9:1 chloroform:acetonitrile, 5% phosphoric acid in methanol treated silica). The solid was then recrystallized in 2:1 benzen:hexane to provide the product as white crystals (1.83 g, 33%), m.p. 143°-145° C. (dec.).

Workup

  1. extractionextracted with ether (2×300 mL)
  2. washwashed with saturated aqueous sodium chloride (1×100 mL)
  3. dry with materialdried with magnesium sulfate
  4. customthe ether was removed
  5. filtrationThe precipitate was collected by suction filtration
  6. washwashed with water (2×25 mL)
  7. customdried
  8. customflash chromatographed
  9. addition(9:1 chloroform:acetonitrile, 5% phosphoric acid in methanol treated silica)
  10. customThe solid was then recrystallized in 2:1 benzen

Sources & evidence

ORD record
ord-f1b91a4551d646419bf74d33d466f5de
Source dataset
uspto-grants-1989_06
Patent number
US04843062

Reaction notes

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