4-Chlorobenzenesulfonyl chloride → cis-Methyl 2-(4-chlorophenylsulfonamido)cycloheptanecarboxylate
Reaction equation
[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]=1Participants
Procedure
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.
Workup
- customThe reaction was partitioned between 100 mL diethyl ether and 100 mL water
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated
- custompurified by flash chromatography on 120 g silica gel with 0 to 30% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-87ce550bb685421b81a9e51ae01d1557
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977362B2
Reaction notes
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