Allyl bromide → HCID 118482913, compound

HRID 2272876Notes

Reaction equation

HRID 2272876 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:23]([N:25]2[C@H:34]([CH2:35][N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26]2)=[O:24])=[C:8]([C:10]2[N:11]3[C:15](=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:17]=2)[CH2:14][C@@H:13]([OH:22])[CH2:12]3)[CH:9]=1.[CH2:42](Br)[CH:43]=[CH2:44]>C1COCC1>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:23]([N:25]2[C@H:34]([CH2:35][N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26]2)=[O:24])=[C:8]([C:10]2[N:11]3[C:15](=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:17]=2)[CH2:14][C@@H:13]([O:22][CH2:44][CH:43]=[CH2:42])[CH2:12]3)[CH:9]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 118482904HCID 118482904, compound

Product 1

HCID 118482913HCID 118482913, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 62 mg (1.54 mmol) of sodium hydride in 8 mL of anhydrous THF cooled to 0° C. there is added a solution of the compound of Step B (820 mg; 1.54 mmol) in THF (6 mL). The suspension is stirred for 15 minutes at 0° C. There is subsequently added 0.15 mL (1.69 mmol) of allyl bromide, dropwise. The reaction mixture is stirred for 5 hours at ambient temperature, and then hydrolysed with a saturated aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic phase is dried over MgSO4, filtered and concentrated to dryness. The oil so obtained is purified by flash chromatography (gradient: dichloromethane/ammoniacal methanol) to yield the title product in solid form.

Workup

  1. stirringThe reaction mixture is stirred for 5 hours at ambient temperature
  2. extractionhydrolysed with a saturated aqueous sodium bicarbonate solution and extracted with dichloromethane
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe oil so obtained
  7. customis purified by flash chromatography (gradient: dichloromethane/ammoniacal methanol)

Sources & evidence

ORD record
ord-fc4482c4e4f4460f8f72c72d83366448
Source dataset
uspto-grants-2015_09
Patent number
US09120791B2

Reaction notes

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