Dicyclohexylcarbodiimide → (3S, 4R)3-[(R)-1-t-Butyldimethylsilyloxyethyl]-4-([2-(p-nitrobenzyloxycarbonylamino)ethylthio]carbonyl-methyl)-2-azetidinone

HRID 342284

Reaktionsgleichung

Reaktionsgleichung von HRID 342284
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16]([OH:18])=O)[NH:13][C:12]1=[O:19])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N+:20]([C:23]1[CH:36]=[CH:35][C:26]([CH2:27][O:28][C:29]([NH:31][CH2:32][CH2:33][SH:34])=[O:30])=[CH:25][CH:24]=1)([O-:22])=[O:21].C1(N=C=NC2CCCCC2)CCCCC1>C1C=CC=CC=1.CN(C)C1C=CN=CC=1>[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16]([S:34][CH2:33][CH2:32][NH:31][C:29]([O:28][CH2:27][C:26]2[CH:35]=[CH:36][C:23]([N+:20]([O-:22])=[O:21])=[CH:24][CH:25]=2)=[O:30])=[O:18])[NH:13][C:12]1=[O:19])[CH3:10])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 3017625(4-Nitrophenyl)methyl (2-mercaptoethyl)carbamateHCID 10859145(3S,4R)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-carboxymethyl-2-oxoazetidine

Produkt 1

HCID 13219828(3S, 4R)3-[(R)-1-t-Butyldimethylsilyloxyethyl]-4-([2-(p-nitrobenzyloxycarbonylamino)ethylthio]carbonyl-methyl)-2-azetidinoneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

1.00 9 (3,48 mmole) of (3S, 4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-4-carboxymethyl-2-azetidinone and 1.07 g (4.8 mmole) of 2-(p-nitrobenzyloxycarbonyl-amino)ethanethiol were dissolved in 20 ml of benzene. To this solution were added 861 mg (4.18 mmole) of dicyclohexylcarbodiimide and 10 mg (0.082 mmole) of 4-dimethylaminopyridine, at room temperature with stirring. The mixture was stirred for 2 hours, after which the insolubles which had formed were filtered off and the resulting filtrate was concentrated to dryness by evaporation under reduced pressure, The residue was purified by column chromatography through 40 g of silica gel, to give 1.59 g (yield 87%) of the desired product as an oil from the fractions eluted with a 1:1 volume mixture of benzene and ethyl acetate.

Aufarbeitung

  1. stirringThe mixture was stirred for 2 hours
  2. customafter which the insolubles which had formed
  3. filtrationwere filtered off
  4. concentrationthe resulting filtrate was concentrated to dryness by evaporation under reduced pressure
  5. customThe residue was purified by column chromatography through 40 g of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4e0b1971d8f14a3cae8d4741d6dd1082
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856556

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