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

HRID 1264478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1264478
[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

Komponenten

7

Edukt 5

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

Produkt 1

HCID 9884459(2S)-[3-(3-Pyridyl)-1-propyl]-1-[(1,5-dimethylpyrazol-3-yl)carbonyl]azetidine-2-carboxylateAusbeute 279,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-4eb6ce82e4334372be1f271749aaccc2
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06544976B1

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