Methanol--water (1/1) → HCID 57489504, compound

HRID 1961551Notes

Reaction equation

HRID 1961551 reaction equation
[O-]I(=O)(=O)=O.[Na+].C[OH:8].O.[Cl:10][C:11]1[CH:12]=[C:13]([C:19]2([C:40]([F:43])([F:42])[F:41])[O:23][N:22]=[C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4([F:39])[CH2:33][N:32]([C:34](=[O:38])[CH2:35][S:36][CH3:37])[CH2:31]4)=[CH:26][CH:25]=3)[CH2:20]2)[CH:14]=[C:15]([Cl:18])[C:16]=1[F:17]>CO>[Cl:10][C:11]1[CH:12]=[C:13]([C:19]2([C:40]([F:41])([F:42])[F:43])[O:23][N:22]=[C:21]([C:24]3[CH:25]=[CH:26][C:27]([C:30]4([F:39])[CH2:33][N:32]([C:34](=[O:38])[CH2:35][S:36]([CH3:37])=[O:8])[CH2:31]4)=[CH:28][CH:29]=3)[CH2:20]2)[CH:14]=[C:15]([Cl:18])[C:16]=1[F:17]

Participants

5

Reactant 3

HCID 22242641Methanol--water (1/1)HCID 23667635Sodium periodateHCID 57489442HCID 57489442, compound

Product 1

HCID 57489504HCID 57489504, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of sodium (meta)periodate (49 mg, 0.23 mmol) in 1:1 methanol/water (6 mL) was cooled with a ice bath and a solution of 1-(3-(4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-3-fluoroazetidin-1-yl)-2-(methylthio)ethanone (102 mg, 0.19 mmol) in methanol (˜2 mL) was added drop wise via pipette. A precipitate forms and the reaction was allowed to stir with the ice bath in place slowly warming to ambient overnight. When complete, the reaction was partitioned between water (5 mL) and CH2Cl2 (5 mL). Aqueous extracted with additional CH2Cl2 (2×5 mL). Organic phase collected and condensed. The crude material was adsorbed on silica and chromatographed on a 12 g silica column, eluting with a gradient of 0% to 100% ethyl acetate in heptane. Fractions containing the desired material were combined and concentrated. CH2Cl2 (˜100 μL) was added to the resulting film. Placing the flask on high vacuum overnight resulted in formation of a white foam. Yield 90 mg (86%). LC/MS retention time=3.317 minutes, MS calculated for (C22H17Cl2F5N2O3S), 554.03; found 555.0 M+H+.

Workup

  1. temperatureslowly warming to ambient overnight
  2. customWhen complete, the reaction was partitioned between water (5 mL) and CH2Cl2 (5 mL)
  3. extractionAqueous extracted with additional CH2Cl2 (2×5 mL)
  4. customOrganic phase collected
  5. customcondensed
  6. customchromatographed on a 12 g silica column
  7. washeluting with a gradient of 0% to 100% ethyl acetate in heptane
  8. additionFractions containing the desired material
  9. concentrationconcentrated
  10. additionCH2Cl2 (˜100 μL) was added to the resulting film
  11. customon high vacuum overnight
  12. customresulted in formation of a white foam

Sources & evidence

ORD record
ord-7d204ae4f5f14142a2a1332935e154a0
Source dataset
uspto-grants-2013_04
Patent number
US08415310B2

Reaction notes

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