Dichloromethane → HCID 178501248, 화합물

HRID 926031

반응식

HRID 926031 반응식
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4]1.C(N(CC)CC)C.ClCCl.Cl[S:24]([C:27]1[CH:28]=[C:29]([CH:39]=[CH:40][CH:41]=1)[C:30]([O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])=[O:31])(=[O:26])=[O:25]>N1C=CC=CC=1>[CH3:12][O:11][C:9]([C@H:6]1[CH2:5][CH2:4][C@H:3]([NH:2][S:24]([C:27]2[CH:28]=[C:29]([CH:39]=[CH:40][CH:41]=2)[C:30]([O:32][CH2:33][CH2:34][Si:35]([CH3:36])([CH3:37])[CH3:38])=[O:31])(=[O:25])=[O:26])[CH2:8][CH2:7]1)=[O:10]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 866763342-(Trimethylsilyl)ethyl 3-(chlorosulfonyl)benzoateHCID 178501210HCID 178501210, 화합물

생성물 1

HCID 178501248HCID 178501248, 화합물수율 92.3%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A mixture of 604 mg of methyl trans-4-aminocyclohexane 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, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 1.27 g of 2-(trimethylsilyl)ethyl 3-{[trans-4-(methoxycarbonyl)cyclohexyl]sulfamoyl}benzoate as a colorless oily substance.

후처리

  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 obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-2db04d9ff51841d99a32c28be3946c70
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284295B2

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