Potassium Carbonate → HCID 86640932, compound

HRID 1271510Notes

Reaction equation

HRID 1271510 reaction equation
S(O)(=O)(=O)C.[CH2:6]1[CH:15]2[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14]2)[CH2:9][CH2:8][NH:7]1.[C:16](=[O:19])([O-:18])[O-].[K+].[K+].[SH:22][C:23]1[C:24]([C:33]([O:35][CH3:36])=[O:34])=[CH:25][C:26]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2.[CH3:37]CCCCC.[C:43]([O:46][CH2:47][CH3:48])(=[O:45])C>CC(C)=O>[CH3:36][O:35][C:33]([C:24]1[C:23]([S:22][C@H:12]2[CH2:13][CH2:14][C@@H:15]3[C@@H:10]([CH2:9][C@@H:8]([C:43]([O:46][CH2:47][CH3:48])=[O:45])[N:7]([C:16]([O:18][CH3:37])=[O:19])[CH2:6]3)[CH2:11]2)=[CH:32][C:31]2[C:26]([CH:25]=1)=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:34]

Participants

6

Reactant 4

HCID 11430Potassium Carbonate2×HCID 13834857HCID 13834857, compound2×HCID 18452906HCID 18452906, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 86640932HCID 86640932, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Procedure

To a solution of decahydroisoquinoline mesylate from preparation 3 (76 mg, 0.21 mmol) in acetone (0.5 mL), potassium carbonate solid (29 mg, 0.21 mmol) was added under nitrogen, followed by addition of a solution of thiol from step B (45 mg, 0.21 mmol) in acetone (0.5 mL) under nitrogen, and the resulting yellow suspension stirred under reflux for 7 h. More potassium carbonate solid (29 mg, 0.21 mmol) and more thiol from step B (45 mg, 0.21 mmol) in acetone (0.5 mL) were added and the mixture stirred under reflux overnight. The reaction mixture was cooled down and concentrated in vacuo. Flash chromatography (silica gel, hexane-ethyl acetate 2.5:1) gave the desired product (36.5 mg, 36% yield).

Workup

  1. additionwas added under nitrogen
  2. temperatureunder reflux for 7 h
  3. stirringthe mixture stirred
  4. temperatureunder reflux overnight
  5. temperatureThe reaction mixture was cooled down
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6962b47f19a149728296f1b89a79ac5c
Source dataset
uspto-grants-2007_04
Patent number
US07205313B2

Reaction notes

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