tert-Butyldimethylsilyl chloride → HCID 86685119, compound

HRID 1913003Notes

Reaction equation

HRID 1913003 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([O:19][CH3:20])[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]2)=[CH:4][C:3]=1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH3:30])=[C:24]([F:31])[C:23]=1[F:32].[CH3:33][C:34]([Si:37](Cl)([CH3:39])[CH3:38])([CH3:36])[CH3:35]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[Si:37]([O:18][CH2:17][C@H:10]1[O:9][C@:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH3:30])=[C:24]([F:31])[C:23]=3[F:32])[CH:4]=2)([O:19][CH3:20])[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@@H:11]1[OH:16])([C:34]([CH3:36])([CH3:35])[CH3:33])([CH3:39])[CH3:38]

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 68015102HCID 68015102, compound

Product 1

HCID 86685119HCID 86685119, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxy-2,3-difluoro-phenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol 3f (3.0 g, 6.8 mmol) was dissolved in 30 mL pyridine, followed by addition of 4-dimethylamino pyridine (166 mg, 1.36 mmol) and TBSCl (1.23 g, 8.2 mmol) in turn. The reaction mixture was stirred for 16 hours. Thereafter, the reaction mixture was concentrated under reduced pressure before 150 mL ethyl acetate were added. The reaction mixture was washed with saturated copper sulfate solution (100 mL) and saturated sodium chloride solution (100 mL) in turn. The organic extract was combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (2S,3R,4S,5S,6R)-6-[(tert-butyl(dimethyl)silyl)oxymethyl]-2-[4-chloro-3-[(4-ethoxy-2,3-difluoro-phenyl)methyl]phenyl]-2-methoxy-tetrahydro-pyran-3,4,5-triol 3g (3.75 g, white solid), yield: 99.7%.

Workup

  1. concentrationThereafter, the reaction mixture was concentrated under reduced pressure before 150 mL ethyl acetate
  2. additionwere added
  3. washThe reaction mixture was washed with saturated copper sulfate solution (100 mL) and saturated sodium chloride solution (100 mL) in turn
  4. extractionThe organic extract
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-47e193dba6304141bbdf325845a98bcd
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

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