Methanol → HCID 11682139, compound

HRID 2174725Notes

Reaction equation

HRID 2174725 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([C:12]#[C:13][C:14]2[CH:15]=[CH:16][C:17]3[S:23][CH2:22][CH2:21][C:20]([CH3:25])([CH3:24])[C:18]=3[CH:19]=2)=[N:10][CH:11]=1)=[O:5].C[OH:27]>O>[CH2:2]([O:3][C:4](=[O:5])[C:6]1[CH:7]=[CH:8][C:9]([C:12]#[C:13][C:14]2[CH:19]=[C:18]3[C:17](=[CH:16][CH:15]=2)[S:23](=[O:27])[CH2:22][CH2:21][C:20]3([CH3:24])[CH3:25])=[N:10][CH:11]=1)[CH3:1]

Participants

4

Reactant 2

HCID 887MethanolHCID 5381Tazarotene

Product 1

HCID 11682139HCID 11682139, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of tazarotene (10.0 g, 28.5 mmol) in methanol (300 mL) was chilled in an ice water bath to <10° C., and then charged with the dropwise addition of a solution of NaIO4 (9.13 g, 42.7 mmol) in water (100 mL) over 30 minutes. The reaction was allowed to warm to room temperature while stirring for 18 hours, and was then concentrated under reduced pressure to remove as much methanol as possible. The reaction was then diluted with DCM (500 mL) and water (150 mL). The two layers were then separated, and the aqueous layer was extracted with DCM (2×100 mL aliquots). The organic fractions were pooled, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude sulfoxide product was then chromatographed using a DCM:EtOAc solvent system. Yield: 9.00 g (86%).

Workup

  1. temperaturewas chilled in an ice water bath to <10° C.
  2. concentrationwas then concentrated under reduced pressure
  3. customto remove as much methanol as possible
  4. additionThe reaction was then diluted with DCM (500 mL) and water (150 mL)
  5. customThe two layers were then separated
  6. extractionthe aqueous layer was extracted with DCM (2×100 mL aliquots)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude sulfoxide product was then chromatographed

Sources & evidence

ORD record
ord-616121f9829b432a94e4af300d544a88
Source dataset
uspto-grants-2015_06
Patent number
US09062037B2

Reaction notes

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