Triethylamine → HCID 22350965, compound

HRID 747530Notes

Reaction equation

HRID 747530 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][N:8]1[C:12]([CH2:13]O)=[CH:11][S:10][C:9]1=[N:15][C:16](=[O:27])[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[O:25][CH3:26])(=[O:3])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:40]=[N+:41]=[N-:42].[Na+]>CN(C=O)C.O>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][N:8]1[C:12]([CH2:13][N:40]=[N+:41]=[N-:42])=[CH:11][S:10][C:9]1=[N:15][C:16](=[O:27])[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[O:25][CH3:26])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 22350940HCID 22350940, compound

Product 1

HCID 22350965HCID 22350965, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The compound (3.45 g) obtained in the above (2) and triethylamine (976 mg) were dissolved in DMF (35 ml), and thereto was added dropwise methanesulfonyl chloride (0.75 ml) under ice-cooling. The mixture was stirred at the same temperature for 2 hours, and thereto was added sodium azide (627 mg), and the mixture was further stirred for 2 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography [chloroform:methanol (98:2)] to give the title compound (3.48 g) as oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography [chloroform:methanol (98:2)]

Sources & evidence

ORD record
ord-4f8e91f65e8245958bfec61e40db5c9e
Source dataset
uspto-grants-2008_07
Patent number
US07396842B2

Reaction notes

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