Diisopropylethylamine → allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 1464731Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1464731
[C:1]([Si:5]([CH3:28])([CH3:27])[O:6][C@@H:7]([C@H:9]1[C:15](=[O:16])[N:14]2[C@@H:10]1[C@@H:11]([CH3:26])[C:12]([S:23]([CH3:25])=O)=[C:13]2[C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH2:29]([O:32][C:33]([N:35]1[CH2:39][C@@H](S)[CH2:37][C@H:36]1[CH2:41][O:42][CH2:43][CH2:44][F:45])=[O:34])[CH:30]=[CH2:31].C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)C>[CH2:29]([O:32][C:33]([N:35]1[CH2:39][C@@H:25]([S:23][C:12]2[C@H:11]([CH3:26])[C@H:10]3[N:14]([C:15](=[O:16])[C@@H:9]3[C@H:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:28])[CH3:27])[CH3:8])[C:13]=2[C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[CH2:37][C@H:36]1[CH2:41][O:42][CH2:43][CH2:44][F:45])=[O:34])[CH:30]=[CH2:31]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 57241269(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethoxymethyl)-4-mercaptopyrrolidineHCID 86747784allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylsulfinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Produkt 1

HCID 57089568allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateAusbeute 43,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of allyl (4R,5S,6S)-6-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl]-4-methyl-3-methylsulfinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (33 mg) and (2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-mercaptopyrrolidine (21 mg) in N,N-dimethylformamide (1.0 ml) was added diisopropylethylamine (10 mg). After stirring for 2 hours at ambient temperature, the solution was diluted with diethyl ether (10 ml) and washed with water, 1N hydrochloric acid, aqueous sodium bicarbonate solution and brine, dried, and evaporated under reduced pressure. The residue was purified by preparative thin layer chromatography [ethyl acetate-n-hexane (1:1.5, V/V)] to give allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)pyrrolidin-4-ylthio]-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (21 mg).

Aufarbeitung

  1. washwashed with water, 1N hydrochloric acid, aqueous sodium bicarbonate solution and brine
  2. customdried
  3. customevaporated under reduced pressure
  4. customThe residue was purified by preparative thin layer chromatography [ethyl acetate-n-hexane (1:1.5, V/V)]

Quellen und Nachweise

ORD-Eintrag
ord-527a11e1bcbc41588fcf0a300e563824
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05306816

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