Cyclopropanecarbonyl chloride → HCID 23144340, compound

HRID 1967804Notes

Reaction equation

HRID 1967804 reaction equation
[CH2:1]([C:4]([C:6]1[S:10][C:9]([NH2:11])=[N:8][C:7]=1[C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)=[O:5])[CH2:2][CH3:3].[CH:17]1([C:20](Cl)=[O:21])[CH2:19][CH2:18]1.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[C:4]([C:6]1[S:10][C:9]([NH:11][C:20]([CH:17]2[CH2:19][CH2:18]2)=[O:21])=[N:8][C:7]=1[C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)(=[O:5])[CH2:1][CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 86060982HCID 86060982, compound

Product 1

HCID 23144340HCID 23144340, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 384 (79.8 mg, 0.338 mmol) and N,N-dimethylaminopyridine (2.10 mg, 0.0172 mmol) were dissolved in pyridine (1.5 mL), and cyclopropanecarbonyl chloride (0.0521 mL, 0.570 mmol) was added thereto under ice-cooling, followed by stirring at room temperature for 5.5 hours. Aqueous saturated sodium hydrogencarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was recrystallized from ethanol to afford the entitled Compound 385 (57.1 mg, 55%) as a white solid.

Workup

  1. temperatureunder ice-cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-193573fb2be24a51a85ed76bed62b7a5
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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