Dichloromethane → HCID 178501219, compound

HRID 1025423Notes

Reaction equation

HRID 1025423 reaction equation
Cl.[CH:2]([NH:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([O:14][CH3:15])=[O:13])[CH2:8][CH2:7]1)([CH3:4])[CH3:3].C(N(CC)CC)C.ClCCl.Cl[S:27]([C:30]1[CH:31]=[C:32]([CH:42]=[CH:43][CH:44]=1)[C:33]([O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])=[O:34])(=[O:29])=[O:28]>N1C=CC=CC=1>[CH:2]([N:5]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([O:14][CH3:15])=[O:13])[CH2:8][CH2:7]1)[S:27]([C:30]1[CH:31]=[C:32]([CH:42]=[CH:43][CH:44]=1)[C:33]([O:35][CH2:36][CH2:37][Si:38]([CH3:39])([CH3:40])[CH3:41])=[O:34])(=[O:28])=[O:29])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 866763342-(Trimethylsilyl)ethyl 3-(chlorosulfonyl)benzoateHCID 178501217HCID 178501217, compound

Product 1

HCID 178501219HCID 178501219, compoundYield 20.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 734 mg of methyl trans-4-(isopropylamino)cyclohexane carboxylate hydrochloride, 0.90 mL of triethylamine, and 10 mL of dichloromethane was stirred at room temperature for 30 minutes, and 10 mL of pyridine and 1.00 g of 2-(trimethylsilyl)ethyl 3-(chlorosulfonyl)benzoate were added thereto in this order, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and to the residue was added an aqueous citric acid solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 311 mg of 2-(trimethylsilyl)ethyl 3-{isopropyl[trans-4-(methoxycarbonyl)cyclohexyl]sulfamoyl}benzoate as a pale yellow solid. ESI+: 484

Workup

  1. stirringby stirring at room temperature overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionto the residue was added an aqueous citric acid solution
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1bed6d56e6e64c50b9ed0e21d0c348c3
Source dataset
uspto-grants-2014_05
Patent number
US08729068B2

Reaction notes

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