Triethylamine → HCID 86597765, compound

HRID 1163338Notes

Reaction equation

HRID 1163338 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:33][C@H:32]([CH2:34]O)[O:31][C:30]4=[O:36])=[CH:25][C:24]=3[F:37])[CH2:19][CH2:18]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:50]=[N+:51]=[N-:52].[Na+]>ClCCl.O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:33][C@H:32]([CH2:34][N:50]=[N+:51]=[N-:52])[O:31][C:30]4=[O:36])=[CH:25][C:24]=3[F:37])[CH2:19][CH2:18]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 67274349HCID 67274349, compound

Product 1

HCID 86597765HCID 86597765, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.67 g 4-{4-[2-fluoro-4{(5R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl}-phenyl]-piperazin-1-yl}-piperidin-1-carboxylic acid benzyl ester (7.16 mmol) and 1.99 ml of triethylamine (14.3 mmol) in 50 ml dichloromethane was added at 0° C. 0.66 ml of methansulfonyl chloride (8.59 mmol). The reaction was stirred at room temperature and monitored by TLC. The reaction was diluted with water and washed with water and brine. The org. layer was dried over Mg sulfate, filtered and evaporated. The oily residue was dissolved in 15 ml DMF. 100 mg of tetrabutyl ammonium iodide and 0.930 g sodium azide (14.32 mmol) were added and the mixture stirred under nitrogen at 80° C. The reaction was monitored by TLC. The DMF was evaporated, the residue dissolved in ethyl acetate and washed with water and brine. The org. layer was dried over Mg sulfate, filtered and evaporated. The residue was crystallized from an ethyl acetate/ether mixture.

Workup

  1. washwashed with water and brine
  2. dry with materiallayer was dried over Mg sulfate
  3. filtrationfiltered
  4. customevaporated
  5. dissolutionThe oily residue was dissolved in 15 ml DMF
  6. stirringthe mixture stirred under nitrogen at 80° C
  7. customThe DMF was evaporated
  8. dissolutionthe residue dissolved in ethyl acetate
  9. washwashed with water and brine
  10. dry with materiallayer was dried over Mg sulfate
  11. filtrationfiltered
  12. customevaporated
  13. customThe residue was crystallized from an ethyl acetate/ether mixture

Sources & evidence

ORD record
ord-163f3dbb867443d5b6047193447b1743
Source dataset
uspto-grants-2010_10
Patent number
US07820823B2

Reaction notes

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