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

HRID 989494ノート

反応式

HRID 989494 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(+,−) 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.

後処理

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

出典と根拠

ORDレコード
ord-8fdec11e57b74e7fb542d1b1d4f702aa
出典データセット
uspto-grants-2003_10
特許番号
US06639107B1

反応ノート

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