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

HRID 1264478노트

반응식

HRID 1264478 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(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).

후처리

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

출처 및 근거

ORD 기록
ord-4eb6ce82e4334372be1f271749aaccc2
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06544976B1

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