Heptane → HCID 86663500, compound

HRID 1950716Notes

Reaction equation

HRID 1950716 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:31]([F:34])([F:33])[F:32])[O:14][N:13]=[C:12]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]([C:25]([NH:27][CH2:28][CH2:29][OH:30])=[O:26])=[CH:17][CH:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCCCCCC.C([O-])(O)=O.[Na+]>CCOC(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:31]([F:32])([F:34])[F:33])[O:14][N:13]=[C:12]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]([C:25]([NH:27][CH2:28][CH:29]=[O:30])=[O:26])=[CH:17][CH:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8]

Participants

7

Reactant 4

HCID 8900HeptaneHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86663499HCID 86663499, compound

Product 1

HCID 86663500HCID 86663500, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-hydroxyethyl)-1-naphthamide (Preparation 8, 730 mg, 1.4 mmol) in EtOAc (100 mL) was added Dess-Martin reagent (725 mg, 1.7 mmol). The reaction was stirred at room temperature for 2 hours. TLC 65:35 EtOAc:heptane shows complete conversion to less polar spot. 50 mL NaHCO3 was added to reaction mixture and stirred for 15 minutes. Contents were diluted with water, extracted with EtOAc (2×75 mL), dried (Na2SO4), and concentrated under vacuum to afford the intermediate (713 mg, 98%) as a solid. m/z (Cl) 513 [M+H]+.

Workup

  1. stirringstirred for 15 minutes
  2. extractionextracted with EtOAc (2×75 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dfb76f34e13e49c3a00f2258faa3f6d9
Source dataset
uspto-grants-2013_03
Patent number
US08404649B2

Reaction notes

Loading…