Diisopropylcarbodiimide → (2S)-[3-(3-Pyridyl)-1-propyl]-1-[(1,5-dimethylpyrazol-3-yl)carbonyl]azetidine-2-carboxylate

HRID 1264478ノート

反応式

HRID 1264478 の反応式
[NH:1]1[CH2:4][CH2:3][CH:2]1[C:5]([OH:7])=[O:6].[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH2:15][CH2:16]O)[CH:9]=1.C(N=[C:22]=[N:23][CH:24]([CH3:26])[CH3:25])(C)C.[C:27]12(CS(O)(=O)=O)C(C)(C)C(CC1)C[C:28]2=[O:29].C[N:43](C1C=CC=CN=1)C>ClCCl>[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH2:15][CH2:16][O:6][C:5]([C@@H:2]2[CH2:3][CH2:4][N:1]2[C:28]([C:27]2[CH:26]=[C:24]([CH3:25])[N:23]([CH3:22])[N:43]=2)=[O:29])=[O:7])[CH:9]=1

参加物

7

反応物 5

HCID 12734DiisopropylcarbodiimideHCID 17288Azetidinecarboxylic AcidHCID 178613-PyridinepropanolHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 218852-Dimethylaminopyridine

生成物 1

HCID 9884459(2S)-[3-(3-Pyridyl)-1-propyl]-1-[(1,5-dimethylpyrazol-3-yl)carbonyl]azetidine-2-carboxylate収率 279.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(2S)-1-(1,5-dimethylpyrazol-3-yl)carbonyl]azetidine-2-carboxylic acid (129.6 mg, 0.58 mmol, 1.0 eq) was dissolved in dry dichloromethane (10 mL), to which was added 3-(3-pyridyl)-1 -propanol (80 μL, 0.62 mmol, 1.07 eq), diisopropylcarbodiimide (140 μL, 0.89 mmol, 1.53 eq), camphorsulfonic acid (46.3 mg, 0.2 mmol, 0.34 eq) and dimethylaminopyridine (29.2 mg, 0.24 mmol, 0.48 eq) in that order. The mixture was stirred at about room temperature for about 15 hours under argon. The solid was filtered off and washed with dichloromethane. The organic filtrate was concentrated and the residue was subjected to flash chromatography (1-10% methanol in chloroform) to give 191.6 mg (96% yield) of the product as a colorless oil. 1H NMR (CDCl3) δ 1.78-2.82 (series of m and s, 9H); 3.61-3.82 (series of s, 3H); 3.82-4.74 (series of m, 4H); 4.89 and 5.32 (dd, 1H, J=10.3, 6.0, J=10.3, 6.0); 6.50-6.57 (series of s, 1H); 7.18-7.24 (m, 1H); 7.40 and 7.54 (d, 1H, J=7.7, J=7.7); 8.28-8.49 (series of nd, 2H).

後処理

  1. filtrationThe solid was filtered off
  2. washwashed with dichloromethane
  3. concentrationThe organic filtrate was concentrated

出典と根拠

ORDレコード
ord-4eb6ce82e4334372be1f271749aaccc2
出典データセット
uspto-grants-2003_04
特許番号
US06544976B1

反応ノート

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