Triethylamine → HCID 118120842, compound

HRID 1508666Notes

Reaction equation

HRID 1508666 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][N:10]=[CH:11][CH:12]([S:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[CH2:13][CH:14]([OH:16])[CH3:15].[CH3:24][S:25](Cl)(=[O:27])=[O:26].C(OCC)(=O)C>O1CCCC1.O>[CH3:24][S:25]([O:16][CH:14]([CH2:13][CH:12]([S:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[CH:11]=[N:10][O:9][CH3:8])[CH3:15])(=[O:27])=[O:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 118120854HCID 118120854, compound

Product 1

HCID 118120842HCID 118120842, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
15 °C

Procedure

1.2 mL of triethylamine was added to a solution of 1.7 g of 5-(methoxyimino)-4-(pyridin-2-ylsulfanyl)pentan-2-ol in 7.0 mL of tetrahydrofuran, and thereafter, 602 μL of methanesulfonyl chloride was added to the mixture at a temperature of 0° C. to 10° C. The thus obtained mixture was stirred at a temperature of 15° C. or lower for 1.5 hours. Thereafter, 50 mL of ethyl acetate and 50 mL of water were added to the reaction mixture, and the water layer was then removed. The organic layer was washed with a saturated sodium chloride aqueous solution, and was then dried over anhydrous magnesium sulfate. After that, the solvent was distilled away under reduced pressure, so as to obtain 2.12 g of 5-(methoxyimino)-4-(pyridin-2-ylsulfanyl)pentan-2-yl methanesulfonate in the form of a brown oily product.

Workup

  1. customthe water layer was then removed
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialwas then dried over anhydrous magnesium sulfate
  4. distillationAfter that, the solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-b00e7f86546f4954809ac36e2bd0f381
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

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