Methanesulfonic Acid → HCID 118377808, compound

HRID 1055598Notes

Reaction equation

HRID 1055598 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]2[CH:17]=[C:18]([C@@:23]3([OH:50])[C@H:28]([O:29][Si](C)(C)C)[C@@H:27]([O:34][Si](C)(C)C)[C@H:26]([O:39][Si](C)(C)C)[C@@H:25]([CH2:44][O:45][Si](C)(C)C)[O:24]3)[CH:19]=[CH:20][C:21]=2[Cl:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:51]S(O)(=O)=O.C(=O)(O)[O-].[Na+]>O1CCCC1.CO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]2[CH:17]=[C:18]([C@@:23]3([O:50][CH3:51])[C@H:28]([OH:29])[C@@H:27]([OH:34])[C@H:26]([OH:39])[C@@H:25]([CH2:44][OH:45])[O:24]3)[CH:19]=[CH:20][C:21]=2[Cl:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 131736394HCID 131736394, compound

Product 1

HCID 118377808HCID 118377808, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,3R,4S,5R,6R)-2-[3-[(4-benzyloxyphenyl)methyl]-4-chloro-phenyl]-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)tetrahydropyran-2-ol 25d in anhydrous tetrahydrofuran was added a solution of methylsulfonic acid (0.2 mL, 2.82 mmol) in methanol (20 mL) at −78° C. The mixture was warmed up to room temperature and stirred for 12 hours. The reaction mixture was neutralized with saturated aqueous sodium bicarbonate till pH becomes 6-7 and extracted with ethyl acetate (50 mL×4). The combined organic layers were washed with water (60 mL×2) and saturated aqueous sodium chloride (60 mL×2) in turn, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by re-crystallization from a toluene/n-hexane mixture ((v/v)=1/20, 500 mL) to give the title compound 25e as a white solid (1.28 g, 54.5%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 545.3[M+HCOO]−.

Workup

  1. extractionextracted with ethyl acetate (50 mL×4)
  2. washThe combined organic layers were washed with water (60 mL×2) and saturated aqueous sodium chloride (60 mL×2) in turn
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by re-crystallization from a toluene/n-hexane mixture ((v/v)=1/20, 500 mL)

Sources & evidence

ORD record
ord-5d65bf0ca4ff44f3b0a5de2760490209
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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