Triethylamine → HCID 86650570, compound

HRID 1971641Notes

Reaction equation

HRID 1971641 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]#[C:7][CH2:8][CH2:9][OH:10].C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(OCC)C.O.C([O-])([O-])=O.[K+].[K+]>[CH3:18][S:19]([O:10][CH2:9][CH2:8][C:7]#[C:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)(=[O:21])=[O:20]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 12181232289652-61-5

Product 1

HCID 86650570HCID 86650570, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 11430Potassium CarbonateSolvent

Procedure

To a solution of 750 mg of 1a and 1 ml of triethyl amine in 15 ml of diethyl ether, was added dropwise at 0° C. 400 μl of methanesulfonyl chloride in 5 ml of diethyl ether. The reaction mixture was stirred for ½ hr and then diluted with 30 ml of water and 5 ml of 1M K2CO3. The product was extracted with diethyl ether and the combined extracts were once washed with water, dried and concentrated, to provide 1.2 g of mesylate 1b; Rf 0.50 (heptane/ethyl acetate 1/1), MS-ESI: [M+1] 231.07.

Workup

  1. extractionThe product was extracted with diethyl ether
  2. washthe combined extracts were once washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ae612784de834811b7baec4812629927
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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