Triethylamine → HCID 86677163, compound

HRID 1429398Notes

Reaction equation

HRID 1429398 reaction equation
[OH:1][CH:2]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9].CCN(CC)CC.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>>[CH3:30][S:31]([O:1][CH:2]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])(=[O:33])=[O:32]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67386725HCID 67386725, compound

Product 1

HCID 86677163HCID 86677163, compoundYield 101.1%

Procedure

To a solution of 30d (2.27 g, 7.62 mmol) and Et3N (2.12 mL, 15.2 mmol), MsCl (1.2 mL, 15.2 mmol) was added dropwise at 0° C. After addition was complete, the reaction was stirred at rt until LC-MS analysis indicated the total consumption of the SM. The solvent was removed and the residue was purified by CC using PE:EA=5:1 as mobile phase to afford the desired product (2.9 g, quant.)

Workup

  1. additionAfter addition
  2. customthe total consumption of the SM
  3. customThe solvent was removed
  4. customthe residue was purified by CC

Sources & evidence

ORD record
ord-beb5ca5713ad45dd8e684bf0b6e2e50f
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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