Hydrochloric Acid → HCID 86745328, Verbindung

HRID 1461603Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1461603
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C:13]([C@H:15]1[N:18]([CH:19]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[C:17](=[O:38])[C@@H:16]1[C@H:39]([O:41][C:42]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43])[CH3:40])=[CH2:14].Cl>ClCCl.O.C(N(CC)CC)C>[CH:12]([C:13]([C@H:15]1[N:18]([CH:19]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH2:29][C:30]2[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=2)[C:17](=[O:38])[C@@H:16]1[C@H:39]([O:41][C:42]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43])[CH3:40])=[CH2:14])=[O:11]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 67796345HCID 67796345, Verbindung

Produkt 1

HCID 86745328HCID 86745328, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel3×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of oxalyl chloride (8.5 ml) in dry dichloromethane (212 ml) was added dropwise a mixture of dimethylsulfoxide (14.5 ml) and dichloromethane (42.5 ml) at -50° C., and the resultant mixture was stirred for 10 minutes at the same temperature as above. A solution of (3S,4S)-4-(1-hydroxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone (45 g) in dry dichloromethane (400 ml) was added dropwise thereto at -50° C. or less over a period of 15 minutes, followed by stirring for 15 minutes. Triethylamine (64 ml) was then dropwise added thereto, and the reaction mixture was warmed to room temperature, diluted with cold water (480 ml) and acidified with 6 N hydrochloric acid (65 ml). The organic layer was washed successively with brine (200 ml×3), 2% sodium bicarbonate (200 ml) and then brine (200 ml) and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate in vacuo gave (3S,4S)-4-(1-formylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone.

Aufarbeitung

  1. washThe organic layer was washed successively with brine (200 ml×3), 2% sodium bicarbonate (200 ml)
  2. dry with materialbrine (200 ml) and dried over anhydrous sodium sulfate
  3. filtrationFiltration and concentration of the filtrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-aedc6c34f5314525bc05d5e06740e56f
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05075435

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