tert-Butyldimethylsilyl chloride → HCID 86685157, compound

HRID 1913060Notes

Reaction equation

HRID 1913060 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH2:13][C:14]3[CH:15]=[C:16]([C@@:21]4([O:32][CH3:33])[C@H:26]([OH:27])[C@@H:25]([OH:28])[C@H:24]([OH:29])[C@@H:23]([CH2:30][OH:31])[O:22]4)[CH:17]=[CH:18][C:19]=3[CH3:20])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:34][C:35]([Si:38](Cl)([CH3:40])[CH3:39])([CH3:37])[CH3:36]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:35]([Si:38]([CH3:40])([CH3:39])[O:31][CH2:30][C@H:23]1[O:22][C@:21]([C:16]2[CH:17]=[CH:18][C:19]([CH3:20])=[C:14]([CH2:13][C:11]3[S:12][C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)=[CH:9][CH:10]=3)[CH:15]=2)([O:32][CH3:33])[C@H:26]([OH:27])[C@@H:25]([OH:28])[C@@H:24]1[OH:29])([CH3:37])([CH3:36])[CH3:34]

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 67157964(2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)Methyl)-4-Methylphenyl)-tetrahydro-6-(hydroxyMethyl)-2-Methoxy-2H-pyran-3,4,5-triol

Product 1

HCID 86685157HCID 86685157, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

(2S,3R,4S,5S,6R)-2-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methyl-phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol 9d (1.8 g, 3.8 mmol) was dissolved in 20 mL pyridine, followed by addition of 4-dimethylamino pyridine (93 mg, 0.76 mmol) and TBSCl (686 mg, 4.55 mmol) in turn. The reaction mixture was stirred for 16 hours. Thereafter, the reaction mixture was concentrated under reduced pressure, dissolved in 30 mL ethyl acetate and was partitioned after 30 mL water were added. The aqueous phase was extracted with ethyl acetate (30 mL×3) and the organic extracts were combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography with elution system A to obtain the title compound (2S,3R,4S,5S,6R)-6-[(tertbutyl(dimethyl)silyl)oxymethyl]-2-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methyl-phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol 9e (2.0 g, orange solid), yield: 89.7%.

Workup

  1. concentrationThereafter, the reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in 30 mL ethyl acetate
  3. customwas partitioned after 30 mL water
  4. additionwere added
  5. extractionThe aqueous phase was extracted with ethyl acetate (30 mL×3)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe resulting residue was purified by silica gel chromatography with elution system

Sources & evidence

ORD record
ord-0bd020a0785547fc98d75a46207f8446
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

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