Allyl bromide → HCID 57722305, compound

HRID 1986551Notes

Reaction equation

HRID 1986551 reaction equation
[H-].[Na+].[CH2:3]1[CH2:7]O[CH2:5][CH2:4]1.[O:8]=[C:9]1[CH:15]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:14][S:13][CH2:12][CH2:11][NH:10]1.[CH2:24](Br)[CH:25]=[CH2:26]>O.CCOC(C)=O>[CH2:26]([N:10]1[C:11]2[CH:5]=[CH:4][CH:3]=[CH:7][C:12]=2[S:13][CH2:14][CH:15]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[C:9]1=[O:8])[CH:25]=[CH2:24]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 15591256(Hexahydro-5-oxo-1,4-thiazepin-6-yl)carbamic acid, (1,1-dimethylethyl) ester

Product 1

HCID 57722305HCID 57722305, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

54 mg of sodium hydride as a 60% suspension (2.24 mmol) are introduced at room temperature into a 100 ml round-bottomed flask, with stirring and under an argon atmosphere, containing 25 ml of THF and 660 mg of 52 (2.24 mmol). The medium is stirred for 1 hour and 452 mg (2.24 mmol) of allyl bromide are then added. The medium is stirred overnight, 25 ml of EtOAc and 25 ml of water are added to the reaction medium and, after separation of the phases by settling, the organic phase is washed with 20 ml of water. The organic phase is dried, filtered and then evaporated to dryness. 0.7 g of crude product is recovered, which product is chromatographed on a silica cartridge (20 g) with a 75/25 heptane/EtOAc mixture. 610 mg of product 56 are recovered (yield=81%).

Workup

  1. stirringThe medium is stirred for 1 hour
  2. stirringThe medium is stirred overnight
  3. customafter separation of the phases
  4. washthe organic phase is washed with 20 ml of water
  5. customThe organic phase is dried
  6. filtrationfiltered
  7. customevaporated to dryness
  8. custom0.7 g of crude product is recovered
  9. customwhich product is chromatographed on a silica cartridge (20 g) with a 75/25 heptane/EtOAc mixture
  10. custom610 mg of product 56 are recovered (yield=81%)

Sources & evidence

ORD record
ord-c129995b32f444279b0c5011455bf75d
Source dataset
uspto-grants-2009_06
Patent number
US07550453B2

Reaction notes

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