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

HRID 1011543ノート

反応式

HRID 1011543 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-87ce550bb685421b81a9e51ae01d1557
出典データセット
uspto-grants-2011_07
特許番号
US07977362B2

反応ノート

読み込み中…