1,2-Dichloroethane → HCID 58286517, 화합물

HRID 2098457노트

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HRID 2098457 반응식
[C@H:1]12[CH2:7][C@H:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[C:24](O)=[O:25].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl.O>[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[C:24]([N:5]1[CH2:6][C@@H:1]2[CH2:7][C@H:4]1[CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:25]

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 2332402-Benzimidazolecarboxylic acidHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane

생성물 1

HCID 58286517HCID 58286517, 화합물수율 63.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

A mixture of 1,1-dimethylethyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (18.3 g, 92.5 mmol), 1H-benzimidazole-2-carboxylic acid, (15.0 g, 92.5 mmol), EDC (21.3 g, 111 mmol), HOBt (2.5 g, 18.5 mmol), NMM (28 g, 277.5 mmol) in CH2Cl2 (250 mL) was stirred at room temperature for 18 h. The reaction was diluted with water and CH2Cl2 then washed with sat. NaHCO3 (200 mL) and brine (200 mL). The solution was dried over anhydrous Na2SO4 and concentrated to give a crude product which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate: 2/1) to give the title compound (20 g) as a white solid. LCMS (m/z): 343.2 (M+H).

후처리

  1. washthen washed with sat. NaHCO3 (200 mL) and brine (200 mL)
  2. dry with materialThe solution was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customto give a crude product which
  5. customwas purified by column chromatography on silica gel (petroleum ether/ethyl acetate: 2/1)

출처 및 근거

ORD 기록
ord-ae0677e762b04f509b11776a5f3bcacf
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450484B2

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