Acetyl chloride → (+,-) Trans N-(2-{4'-[2-(Propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-yl}-ethyl)-acetamide

HRID 989494노트

반응식

HRID 989494 반응식
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C@@H:16]3[CH2:20][CH2:19][CH2:18][C@H:17]3[NH:21][S:22]([CH:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:35](Cl)(=[O:37])[CH3:36]>C(Cl)Cl>[CH3:26][CH:25]([S:22]([NH:21][C@@H:17]1[CH2:18][CH2:19][CH2:20][C@H:16]1[C:13]1[CH:14]=[CH:15][C:10]([C:7]2[CH:6]=[CH:5][C:4]([CH2:3][CH2:2][NH:1][C:35](=[O:37])[CH3:36])=[CH:9][CH:8]=2)=[CH:11][CH:12]=1)(=[O:24])=[O:23])[CH3:27]

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 69112967(+,-) Trans Propane-2-sulfonic Acid {2-[4'-(2-amino-ethyl)-biphenyl-4-yl]-cyclopentyl}-amide

생성물 1

HCID 69113096(+,-) Trans N-(2-{4'-[2-(Propane-2-sulfonylamino)-cyclopentyl]-biphenyl-4-yl}-ethyl)-acetamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(+,−) Trans propane-2-sulfonic acid {2-[4′-(2-amino-ethyl)-biphenyl-4-yl]-cyclopentyl}-amide (prepared in example 9) was dissolved in 20 mL of dry methylene chloride and triethylamine added (0.275 mL, 1.98 mmol). To this stirred mixture was added acetyl chloride (0.084 mL, 1.19 mmol). The reaction was stirred at room temperature for 3 days. The reaction was concentrated in vacuo and chromatographed on a Chromatotron® eluting with 98:2 methylene chloride:methanol which afforded 150 mg (64% 2 steps) of the title compound. The NMR was consistent with the assigned structure.

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. customchromatographed on a Chromatotron®
  3. washeluting with 98:2 methylene chloride

출처 및 근거

ORD 기록
ord-8fdec11e57b74e7fb542d1b1d4f702aa
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06639107B1

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