Methanesulfonic Acid → HCID 68015102, compound

HRID 1055583Notes

Reaction equation

HRID 1055583 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:35])[C@H:13]([O:14][Si](C)(C)C)[C@@H:12]([O:19][Si](C)(C)C)[C@H:11]([O:24][Si](C)(C)C)[C@@H:10]([CH2:29][O:30][Si](C)(C)C)[O:9]2)=[CH:4][C:3]=1[CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH2:44][CH3:45])=[C:39]([F:46])[C:38]=1[F:47].[CH3:48]S(O)(=O)=O.C(=O)(O)[O-].[Na+]>O1CCCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([O:35][CH3:48])[C@H:13]([OH:14])[C@@H:12]([OH:19])[C@H:11]([OH:24])[C@@H:10]([CH2:29][OH:30])[O:9]2)=[CH:4][C:3]=1[CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH2:44][CH3:45])=[C:39]([F:46])[C:38]=1[F:47]

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 131736390HCID 131736390, compound

Product 1

HCID 68015102HCID 68015102, compoundYield 106.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,3R,4S,5R,6R)-2-[4-chloro-3-[(4-ethoxy-2,3-difluoro-phenyl)methyl]phenyl]-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyetetrahydropyran-2-ol 23f (0.97 g, 1.3 mmol) in tetrahydrofuran (10 mL) was added a solution of methylsulfonic acid (0.05 mL, 0.65 mmol) in methanol (2 mL) at −70° C. The mixture was warmed up to room temperature and stirred for 16 hours. The reaction mixture was neutralized with saturated aqueous sodium bicarbonate till pH becomes 6-7 and extracted with ethyl acetate (10 mL×3). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by re-crystallization from a toluene/petroleum ether mixture ((v/v)=1/1, 30 mL) at −5° C. to give the title compound 23g as a pale yellow sticky solid (0.33 g, 54%).

Workup

  1. extractionextracted with ethyl acetate (10 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by re-crystallization from a toluene/petroleum ether mixture ((v/v)=1/1, 30 mL) at −5° C.

Sources & evidence

ORD record
ord-d8dbd190659b45f3b3c95bb20453bec4
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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