Triethylamine → 4-Phenylbutyl 2-[benzylsulfonyl]-perhydropyridazinecarboxylate

HRID 851941ノート

反応式

HRID 851941 の反応式
[C:1]1([CH2:7][S:8](Cl)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:19])[NH:13]1.C(N(CC)CC)C>C(Cl)Cl>[CH2:7]([S:8]([N:13]1[CH:14]([C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:19])[CH2:15][CH2:16][CH2:17][NH:12]1)(=[O:10])=[O:9])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 74740Phenylmethanesulfonyl chlorideHCID 184700714-Phenylbutyl perhydropyridazinecarboxylate

生成物 1

HCID 184700884-Phenylbutyl 2-[benzylsulfonyl]-perhydropyridazinecarboxylate収率 64.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

A solution of α-toluene sulfonyl chloride (1.12 g, 5.77 mmol) in CH2Cl2 was added to a CH2Cl2 solution containing 4-phenylbutyl perhydropyridazinecarboxylate (1.37 g, 5.2 mmol) and triethylamine (0.83 ml, 6 mmol). The reaction was stirred overnight at room temperature under nitrogen atmosphere, and then diluted to 50 ml CH2Cl2. The organic layer was washed with water, dried, and concentrated. The crude material was purified by silica gel column to yield 1.4 g (64%) final product as clear oil. Rf=0.60 (2:1 hexane:EtOAc). 1H NMR (CDCl3, 400 MHz): δ 1.68 (m, 8H); 2.67 (m, 2H); 2.90 (m, 1H); 3.38 (m, 2H); 4.22 (m, 5H); 7.32 (m, 10H). Anal. Calcd. for C22H28N2S1O4: C, 63.44; H, 6.78; N, 6.73, S, 7.70. Found: C, 63.86; H, 6.83; N, 6.41, S, 7.58.

後処理

  1. washThe organic layer was washed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe crude material was purified by silica gel column

出典と根拠

ORDレコード
ord-0f0075878d534f4a9f0888e44873c657
出典データセット
uspto-grants-2007_08
特許番号
US07253169B2

反応ノート

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