Benzyl Bromide → HCID 70494679, compound

HRID 1381152Notes

Reaction equation

HRID 1381152 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[C@@H:17]([OH:18])[C:16](=[O:19])[N:15]([CH2:20][CH2:21][N:22](C(OC(C)(C)C)=O)[CH3:23])[C:14]3[CH:31]=[CH:32][C:33]([Cl:35])=[CH:34][C:13]=3[S:12]2)=[CH:7][CH:6]=1.[CH2:36](Br)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C1C=CC=CC=1.CN(C)C=O.O>[ClH:35].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C@H:11]2[C@@H:17]([O:18][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:16](=[O:19])[N:15]([CH2:20][CH2:21][NH:22][CH3:23])[C:14]3[CH:31]=[CH:32][C:33]([Cl:35])=[CH:34][C:13]=3[S:12]2)=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 86740747HCID 86740747, compound

Product 1

HCID 70494679HCID 70494679, compoundYield 150%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.28 g of sodium hydride (63% oil dispersion) is added to a solution of 1.05 g of (-)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(N-tert.butoxycarbonyl-N-methylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one in a mixture of 10 ml of benzene and one ml of dimethylformamide. The mixture is stirred at room temperature for 30 minutes. Then, 0.92 g of benzyl bromide is added to the mixture, and said mixture is stirred at room temperature for 20 hours. The mixture is diluted with water, and the aqueous mixture is extracted with benzene. The extract is washed with water, dried and evaporated to remove solvent. Then, 7 ml of formic acid and one ml of water are added to the residue (oil: 1.36 g) thus obtained, and the mixture is stirred at 40° C. for 1.5 hours. The mixture is evaporated under reduced pressure to remove solvent. The residue is dissolved in 10% hydrochloric acid, and the solution is washed with ether. The aqueous layer is alkalized with ammonia and extracted with chloroform. The extract is washed with water, dried and evaporated to remove solvent. The residue is converted to its hydrochloride and recrystallized from ethanol. 0.83 g of (+)-cis-2-(4-methoxyphenyl)-3-benzyloxy-5-[2-(N-methylamino)ethyl]-8-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one.hydrochloride is obtained.

Workup

  1. stirringis stirred at room temperature for 20 hours
  2. extractionthe aqueous mixture is extracted with benzene
  3. washThe extract is washed with water
  4. customdried
  5. customevaporated
  6. customto remove solvent
  7. additionThen, 7 ml of formic acid and one ml of water are added to the residue (oil: 1.36 g)
  8. customthus obtained
  9. stirringthe mixture is stirred at 40° C. for 1.5 hours
  10. customThe mixture is evaporated under reduced pressure
  11. customto remove solvent
  12. dissolutionThe residue is dissolved in 10% hydrochloric acid
  13. washthe solution is washed with ether
  14. extractionextracted with chloroform
  15. washThe extract is washed with water
  16. customdried
  17. customevaporated
  18. customto remove solvent
  19. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-cf762a45b13f4754a342cb4555096795
Source dataset
uspto-grants-1986_04
Patent number
US04585768

Reaction notes

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