Benzyl Bromide → HCID 86685127, compound

HRID 1913016Notes

Reaction equation

HRID 1913016 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[O:15][C@:14]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH3:34])=[C:28]([F:35])[CH:27]=3)[CH:19]=2)([O:16][CH3:17])[C@H:13]([OH:36])[C@@H:12]([OH:37])[C@@H:11]1[OH:38])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[CH2:41](Br)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>CN(C)C=O>[CH2:41]([O:38][C@H:11]1[C@H:12]([O:37][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:13]([O:36][CH2:14][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@:14]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH3:34])=[C:28]([F:35])[CH:27]=3)[CH:19]=2)([O:16][CH3:17])[O:15][C@@H:10]1[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 86685126HCID 86685126, compound

Product 1

HCID 86685127HCID 86685127, compoundYield 199.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2S,3R,4S,5S,6R)-6-[(tert-butyl(dimethyl)silyl)oxymethyl]-2-[4-chloro-3-[(4-ethoxy-3-fluoro-phenyl)methyl]phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol 4g (7.14 g, 12.5 mmol) was dissolved in 100 mL N,N-dimethyl formamide, followed by addition of 60% NaH (2.5 g, 62.5 mmol) in an ice bath. The reaction mixture was warmed and stirred for 40 minutes at room temperature. The mixture was stirred for 16 hours after benzyl bromide (7.5 mL, 62.5 mmol) was added. Thereafter, the reaction mixture was concentrated under reduced pressure after 20 mL methanol were added. The residue was dissolved in 200 mL ethyl acetate and 50 mL water and partitioned. The aqueous phase was extracted with ethyl acetate (50 mL). The organic extracts were washed with water (50 mL), then saturated sodium chloride (50 mL), combined, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain the title compound [[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxy-3-fluoro-phenyl)methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methoxy]tert-butyl-dimethylsilane 4h (10.5 g, yellow grease), yield: 99.8%.

Workup

  1. temperatureThe reaction mixture was warmed
  2. additionwas added
  3. concentrationThereafter, the reaction mixture was concentrated under reduced pressure after 20 mL methanol
  4. additionwere added
  5. dissolutionThe residue was dissolved in 200 mL ethyl acetate
  6. custom50 mL water and partitioned
  7. extractionThe aqueous phase was extracted with ethyl acetate (50 mL)
  8. washThe organic extracts were washed with water (50 mL)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-330417a23b124bf2b2e65e6dda8bb177
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

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