Triethylamine → HCID 22163894, compound

HRID 1087807Notes

Reaction equation

HRID 1087807 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:19][OH:20])[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])=[CH:4][CH:3]=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(N(CC)CC)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:19][O:20][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22163887HCID 22163887, compound

Product 1

HCID 22163894HCID 22163894, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 0.99 g of the title compound of Step C and 0.6 ml of methanesulfonyl chloride in 20 ml of THF at 0° C. was added 1.05 ml of triethylamine. The reaction was stirred overnight at room temperature, partitioned between 5% aqueous sodium bicarbonate and chloroform, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel with 30% ethyl acetate/hexane to afford 1.1 g of the title compound as a viscous yellow oil.

Workup

  1. custompartitioned between 5% aqueous sodium bicarbonate and chloroform
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-0b038af22f424744951c3cb6958e2f59
Source dataset
uspto-grants-1990_10
Patent number
US04960784

Reaction notes

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