Triethylamine → HCID 86609879, compound

HRID 1645311Notes

Reaction equation

HRID 1645311 reaction equation
CS(Cl)(=O)=O.[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:24][C@H:23]([CH2:25]O)[O:22][C:21]2=[O:27])=[CH:16][C:15]=1[F:28])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.[N-:36]=[N+:37]=[N-:38].[Na+]>ClCCl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.CCCCCC>[N:36]([CH2:25][C@H:23]1[O:22][C:21](=[O:27])[N:20]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[C:15]([F:28])[CH:16]=2)[CH2:24]1)=[N+:37]=[N-:38]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 57754831HCID 57754831, compound

Product 1

HCID 86609879HCID 86609879, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

4.32 g of methanesulphonyl chloride (MW: 114.55, 37.82 mmol) were added at 10° C., with stirring, to a mixture of 10 g of (5R)-3-(4-benzyloxy-3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one (MW: 317.32, 31.51 mmol) and 4.78 g of triethylamine (MW: 101.19, 47.26 mmol) in 300 ml of dichloromethane. The reaction mixture was stirred at RT for 1 h and the course of the reaction was monitored by TLC (ethyl acetate/hexane 1/1). The reaction was quenched with 100 ml of water and the organic phase was washed with 100 ml of saturated sodium chloride solution. The organic phase was dried over magnesium sulphate and filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in 100 ml of dimethylformamide and 5.12 g of sodium azide (MW: 65.01, 78.7 mmol) and a catalytic amount of tetrabutylammonium iodide was added. The suspension was stirred overnight at 90° C. The course of the reaction was monitored by HPLC. The dimethylformamide was removed under reduced pressure using a rotary evaporator, the residue was dissolved in 200 ml of dichloromethane and the organic phase was washed in succession with 100 ml of water and 100 ml of saturated sodium chloride solution. The dichloromethane solution was dried over magnesium sulphate and filtered, and the filtrate was concentrated under reduced pressure. The residue was crystallised from 150 ml of ethyl acetate/hexane 1/1. Yield: 10.4 g, 97%. MS: 343.1 (M+H)+. Method: ESI+.

Workup

  1. customThe reaction was quenched with 100 ml of water
  2. washthe organic phase was washed with 100 ml of saturated sodium chloride solution
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in 100 ml of dimethylformamide
  7. stirringThe suspension was stirred overnight at 90° C
  8. customThe dimethylformamide was removed under reduced pressure
  9. customa rotary evaporator
  10. dissolutionthe residue was dissolved in 200 ml of dichloromethane
  11. washthe organic phase was washed in succession with 100 ml of water and 100 ml of saturated sodium chloride solution
  12. dry with materialThe dichloromethane solution was dried over magnesium sulphate
  13. filtrationfiltered
  14. concentrationthe filtrate was concentrated under reduced pressure
  15. customThe residue was crystallised from 150 ml of ethyl acetate/hexane 1/1

Sources & evidence

ORD record
ord-e5551d84ac324eee9dc770317fcb6485
Source dataset
uspto-grants-2012_02
Patent number
US08124772B2

Reaction notes

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