4-Chlorobenzenesulfonyl chloride → cis-Methyl 2-(4-chlorophenylsulfonamido)cycloheptanecarboxylate

HRID 1011543노트

반응식

HRID 1011543 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[NH2:13][C@H:14]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]1[C:21]([O:23][CH3:24])=[O:22].C(N(CC)CC)C>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:13][C@H:14]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]2[C:21]([O:23][CH3:24])=[O:22])(=[O:10])=[O:9])=[CH:4][CH:3]=1

참가 물질

4

반응물 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 66658076rac-methyl (1R,2S)-2-aminocycloheptane-1-carboxylate hydrochloride

생성물 1

HCID 67314641cis-Methyl 2-(4-chlorophenylsulfonamido)cycloheptanecarboxylate수율 91.1%

실험 절차

4-Chlorobenzenesulfonylchloride (3.17 g, 15 mmol) was added to a mixture of cis-methyl 2-aminocycloheptanecarboxylate hydrochloride 2.08 g, 10 mmol) and triethylamine (4.2 mL, 30 mmol) and stirred at room temperature for 4 h. The reaction was partitioned between 100 mL diethyl ether and 100 mL water. The organic layer was dried over sodium sulfate, concentrated, and purified by flash chromatography on 120 g silica gel with 0 to 30% ethyl acetate in hexane to yield cis-methyl 2-(4-chlorophenylsulfonamido)cycloheptanecarboxylate (3.15 g, 91%). 1H NMR (400 MHz, CDCl3) δ ppm 7.78-7.81 (1H, m), 7.74-7.78 (1H, m), 7.46-7.48 (1H, m), 7.42-7.46 (1H, m), 5.33 (1H, d, J=9.57 Hz), 3.59 (3H, s), 3.53 (1H, tt, J=9.57, 4.03 Hz), 2.80 (1H, dt, J=8.06, 4.03 Hz), 1.76-1.92 (2H, m), 1.44-1.75 (6H, m), 1.25-1.41 (2H, m). LC/MS R.T.=2.65 min; [M+H]+=346.10; [M+Na]+=368.07; [M−H]−=344.04.

후처리

  1. customThe reaction was partitioned between 100 mL diethyl ether and 100 mL water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. custompurified by flash chromatography on 120 g silica gel with 0 to 30% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-87ce550bb685421b81a9e51ae01d1557
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977362B2

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