Triethylamine → HCID 86643131, compound

HRID 1696709Notes

Reaction equation

HRID 1696709 reaction equation
[OH:1][C@H:2]([CH3:21])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)=[O:4].[CH3:22][S:23](Cl)(=[O:25])=[O:24].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl>[CH3:22][S:23]([O:1][C@H:2]([CH3:21])[C:3]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[CH:9][CH:10]=1)=[O:4])(=[O:25])=[O:24]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 68710189HCID 68710189, compound

Product 1

HCID 86643131HCID 86643131, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (1.53 g, 5.34 mmol) synthesized in the above (3) was dissolved in dichloromethane (15 mL), and with cooling with ice, methanesulfonyl chloride (0.62 mL, 8.0 mmol) and triethylamine (1.11 mL, 8.0 mmol) were added in that order. The reaction solution was stirred for 20 minutes with cooling with ice. The reaction solution was poured into aqueous saturated sodium hydrogencarbonate solution, and extracted with chloroform. The organic layer was washed with aqueous saturated ammonium chloride solution and water in that order, then dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting pale yellow solid was washed with chloroform and n-hexane to obtain the entitled compound (1.8 g, 93%) as a white solid.

Workup

  1. additionwere added in that order
  2. temperaturewith cooling with ice
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with aqueous saturated ammonium chloride solution and water in that order
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. washthe resulting pale yellow solid was washed with chloroform and n-hexane

Sources & evidence

ORD record
ord-0280f111d91d4570b06ada262fb1e9bf
Source dataset
uspto-grants-2012_04
Patent number
US08163770B2

Reaction notes

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