Potassium hydroxy sulfite → HCID 66554478, compound

HRID 1258008Notes

Reaction equation

HRID 1258008 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[Cl:7][C:8]1[CH:9]=[C:10]([C:16]2([C:40]([F:43])([F:42])[F:41])[O:20][N:19]=[C:18]([C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[C:26]3([CH2:32][N:31]([C:33]([CH:35]5[CH2:38]S(=O)[CH2:36]5)=[O:34])[CH2:30]3)[O:25][CH2:24]4)[CH2:17]2)[CH:11]=[C:12]([Cl:15])[C:13]=1[F:14]>O.CO>[Cl:15][C:12]1[CH:11]=[C:10]([C:16]2([C:40]([F:41])([F:43])[F:42])[O:20][N:19]=[C:18]([C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[C:26]3([CH2:32][N:31]([C:33]([CH:35]5[CH2:38][S:3](=[O:5])(=[O:2])[CH2:36]5)=[O:34])[CH2:30]3)[O:25][CH2:24]4)[CH2:17]2)[CH:9]=[C:8]([Cl:7])[C:13]=1[F:14]

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 86670534HCID 86670534, compound

Product 1

HCID 66554478HCID 66554478, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a 20 mL vial containing a solution of oxone (320 mg, 0.52 mmol) in water (2 mL) at 0° C. was added (5′-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-3′H-spiro[azetidine-3,1′-isobenzofuran]-1-yl)(1-oxidothietan-3-yl)methanone from Example 4 (100 mg, 0.17 mmol) as a solution in methanol (4 mL). The reaction was stirred at 0° C. and allowed to warm to room temperature while stirring over 2 hours. Next, the reaction mixture was concentrated to remove excess MeOH and diluted with water. The crude product was extracted with CH2Cl2 (75 mL) and the organic phase was dried (Na2SO4) and concentrated under vacuum. The residue was purified by preparative HPLC to afford the final product (16 mg, 16%) as a solid. 1HNMR (CDCl3) δ ppm: 7.69 (1H), 7.63-7.60 (3H), 7.49 (1H), 5.19 (2H), 4.61-4.45 (4H), 4.36 (2H), 4.24-4.09 (3H), 3.72 (1H), 3.30 (1H); m/z (CI) 593 [M+H]+.

Workup

  1. temperatureto warm to room temperature
  2. stirringwhile stirring over 2 hours
  3. concentrationNext, the reaction mixture was concentrated
  4. customto remove excess MeOH
  5. additiondiluted with water
  6. extractionThe crude product was extracted with CH2Cl2 (75 mL)
  7. dry with materialthe organic phase was dried (Na2SO4)
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-62a2ff4ab4144a67a5e5287a00f925eb
Source dataset
uspto-grants-2013_06
Patent number
US08466115B2

Reaction notes

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