Triethylamine → HCID 178472517, Verbindung

HRID 2242257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2242257
Cl.[CH2:2]([O:4][C:5]([C@H:7]1[CH2:10][C@@H:9]([NH2:11])[CH2:8]1)=[O:6])[CH3:3].C(N(CC)CC)C.[CH2:19]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[O:33][C:32]([C:34]3[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=3)=[N:31][N:30]=2)=[CH:25][CH:24]=1)[CH:20]([CH3:22])[CH3:21].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:19]([C:23]1[CH:24]=[CH:25][C:26]([C:29]2[O:33][C:32]([C:34]3[CH:35]=[CH:36][C:37]([CH2:38][NH:11][C@@H:9]4[CH2:10][C@H:7]([C:5]([O:4][CH2:2][CH3:3])=[O:6])[CH2:8]4)=[CH:40][CH:41]=3)=[N:31][N:30]=2)=[CH:27][CH:28]=1)[CH:20]([CH3:22])[CH3:21]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydride2×HCID 592042884-[5-(4-Isobutylphenyl)-1,3,4-oxadiazol-2-yl]benzaldehydeHCID 178472514HCID 178472514, Verbindung2×

Produkt 1

HCID 178472517HCID 178472517, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of cis-3-amino-cyclobutanecarboxylic acid ethyl ester hydrochloride (0.181 g, 1.01 mmol), triethylamine (0.10 mL, 0.72 mmol) and dichloromethane (8 mL) was stirred at room temperature for 30 minutes. 4-[5-(4-isobutylphenyl)-1,3,4-oxadiazol-2-yl]benzaldehyde (0.181 mg, 1.04 mmol) was added to the reaction mixture and stirred for 2 hours. Sodium triacetoxyborohydride (0.213 g, 1.01 mmol) was added to the reaction mixture and stirred for 16 hours. Additional cis-3-amino-cyclobutanecarboxylic acid ethyl ester hydrochloride (0.100 mg, 0.773 mmol) and sodium triacetoxyborohydride (0.213 g, 1.01 mmol) was added to the reaction mixture and stirred for 72 hours. The reaction mixture was concentrated in vacuo and the resulting residue was triturated with water, filtered and dried to provide the title compound (0.303 g, 88% yield) as a white solid.

Aufarbeitung

  1. stirringstirred for 2 hours
  2. stirringstirred for 16 hours
  3. stirringstirred for 72 hours
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customthe resulting residue was triturated with water
  6. filtrationfiltered
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f91ff40ccba045b4aa7509e4f2fa1e47
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07671043B2

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