Imidazole → HCID 86685119, compound

HRID 1055584Notes

Reaction equation

HRID 1055584 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].[Si:33](Cl)([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34].N1C=CN=C1>ClCCl>[Si:33]([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:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 68015102HCID 68015102, compound

Product 1

HCID 86685119HCID 86685119, compoundYield 107.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (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 23g (9.02 g, 18.95 mmol) in dichloromethane (150 mL) were added tert-butyldimethylsilyl chloride (4.29 g, 28.43 mmol), imidazole (2.58 g, 37.9 mmol) and N,N-dimethylaminopyridine (0.23 g, 1.9 mmol) in turn at 0° C. The mixture was stirred at room temperature for 3 hours, and then washed with water (100 mL×3) and saturated aqueous sodium chloride (100 mL) in turn. The resulting mixture was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 23h as a yellow solid (12.0 g, 100%). This material was not further purified.

Workup

  1. washwashed with water (100 mL×3) and saturated aqueous sodium chloride (100 mL) in turn
  2. dry with materialThe resulting mixture was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e3259b1951e0496ca88036e2bf650105
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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