Triethylamine → HCID 86609879, compound

HRID 2279662Notes

Reaction equation

HRID 2279662 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][C@H:18]([CH2:20]O)[O:17][C:16]2=[O:22])=[CH:11][C:10]=1[F:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:36]=[N+:37]=[N-:38].[Na+]>ClCCl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.CCCCCC>[N:36]([CH2:20][C@H:18]1[O:17][C:16](=[O:22])[N:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:10]([F:23])[CH:11]=2)[CH2:19]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

A solution of 10 g (5R)-3-(4-benzyloxy-3-fluoro-phenyl)-5-hydroxymethyl-oxazolidin-2-one (MW: 317.32, 31.51 mmol) and 4.78 g triethylamine (MW: 101.19, 47.26 mmol) in 300 ml dichloromethane was treated under stirring at 10° C. with 4.32 g of methane sulfonyl chloride (MW: 114.55, 37.82 mmol). The reaction was stirred at room temperature for one hour and monitored by TLC (ethyl acetate:hexane 1:1). The reaction mixture was quenched with 100 ml water and the organic layer washed with 100 ml brine. The organic layer was dried over magnesium sulfate, filtered and the filtrate evaporated under reduced pressure. The residue was dissolved in 100 ml dimethylformamide, 5.12 g sodium azide (MW: 65.01, 78.7 mmol) and a catalytic amount of tetrabutyl ammonium iodide were added. The suspension was stirred at 90° C. over night. The reaction was monitored by HPLC. The dimethylformamide was evaporated under reduced pressure, the residue dissolved in 200 ml dichloromethane and the organic layer washed successively with 100 ml water and 100 ml brine. The dichloromethane solution was dried over magnesium sulfate, filtered, and the filtrate evaporated under reduced pressure. The residue was crystallized from 150 ml of a 1/1 mixture of ethyl acetate:hexane. The crystals were collected to afford an off white solid. Yield: 10.4-g, 97%. MS: 343.1 (M+H)+−. Method: ESI+.

Workup

  1. customThe reaction mixture was quenched with 100 ml water
  2. washthe organic layer washed with 100 ml brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate evaporated under reduced pressure
  6. dissolutionThe residue was dissolved in 100 ml dimethylformamide
  7. stirringThe suspension was stirred at 90° C. over night
  8. customThe dimethylformamide was evaporated under reduced pressure
  9. dissolutionthe residue dissolved in 200 ml dichloromethane
  10. washthe organic layer washed successively with 100 ml water and 100 ml brine
  11. dry with materialThe dichloromethane solution was dried over magnesium sulfate
  12. filtrationfiltered
  13. customthe filtrate evaporated under reduced pressure
  14. customThe residue was crystallized from 150 ml of a 1/1 mixture of ethyl acetate
  15. customThe crystals were collected
  16. customto afford an off white solid

Sources & evidence

ORD record
ord-edee58120bb94ff68e5452df06046c22
Source dataset
uspto-grants-2015_09
Patent number
US09133213B2

Reaction notes

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