Dichloromethane → HCID 178501219, compound

HRID 926034

Reaction equation

HRID 926034 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-eb94420c38534867907ca8e7dd4952e8
Source dataset
uspto-grants-2016_03
Patent number
US09284295B2

Linked notes

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