Benzyl Bromide → HCID 89576927, compound

HRID 1055585Notes

Reaction equation

HRID 1055585 reaction equation
[H-].[Na+].[Si:3]([O:10][CH2:11][C@H:12]1[O:17][C@:16]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH3:36])=[C:30]([F:37])[C:29]=3[F:38])[CH:21]=2)([O:18][CH3:19])[C@H:15]([OH:39])[C@@H:14]([OH:40])[C@@H:13]1[OH:41])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[CH2:42](Br)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:6]([Si:3]([CH3:5])([CH3:4])[O:10][CH2:11][C@@H:12]1[C@@H:13]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C@H:14]([O:40][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@@H:15]([O:39][CH2:16][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@@:16]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH3:36])=[C:30]([F:37])[C:29]=3[F:38])[CH:21]=2)([O:18][CH3:19])[O:17]1)([CH3:9])([CH3:7])[CH3:8]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 86685119HCID 86685119, compound

Product 1

HCID 89576927HCID 89576927, compoundYield 453.1%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (3.18 g, 32.65 mmol, 60% dispersion in Mineral oil) in anhydrous tetrahydrofuran (15 mL) was added a solution of (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-tetrahydropyran-3,4,5-triol 23h (11.16 g, 18.95 mmol) in anhydrous tetrahydrofuran (80 mL) slowly at 0° C. The mixture was stirred at 0° C. for 1 hour, and then benzyl bromide (20.3 mL, 170.55 mmol) was added. The mixture was warmed up to room temperature and tetrabutylammonium iodide (0.70 g, 1.90 mmol) was added. The mixture was stirred for 12 hours. The reaction mixture was quenched with water (100 mL) at 0° C. and extracted with ethyl acetate (100 mL×2). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 23i as yellow oil (36.90 g, 100%). This material was not further purified.

Workup

  1. temperatureThe mixture was warmed up to room temperature
  2. stirringThe mixture was stirred for 12 hours
  3. customThe reaction mixture was quenched with water (100 mL) at 0° C.
  4. extractionextracted with ethyl acetate (100 mL×2)
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6c345c6a23b142e590fe72ca0f75f896
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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