Dicyclohexylcarbodiimide → (3S-trans)-3-[[[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-4-methyl-1-(phenylmethoxy)-2-azetidinone

HRID 484675

Reaktionsgleichung

Reaktionsgleichung von HRID 484675
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]([NH:11][CH:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([OH:15])=O)=[O:10])[C:5](=[O:22])[C:4]1=[O:23])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[NH2:39][C@H:40]1[C@H:43]([CH3:44])[N:42]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]1=[O:53].C1(C)C(S([O-])(=O)=O)=CC=CC=1.C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]([NH:11][CH:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([NH:39][C@H:40]2[C@H:43]([CH3:44])[N:42]([O:45][CH2:46][C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[C:41]2=[O:53])=[O:15])=[O:10])[C:5](=[O:22])[C:4]1=[O:23])[CH3:2]

Komponenten

8

Edukt 5

HCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 3424274ToluenesulfonateHCID 4550893(R)-(-)-alpha-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]benzeneacetic acidHCID 13036842(3S-trans)-3-amino-4-methyl-1-(phenylmethoxy)-2-azetidinone

Produkt 1

HCID 13036845(3S-trans)-3-[[[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-4-methyl-1-(phenylmethoxy)-2-azetidinone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A suspension of α-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]benzeneacetic acid (0.879 g) hydroxybenzotriazole (0.42 g), and dicyclohexylcarbodiimide (0.56 g), in dimethylformamide (15 ml) is stirred at 26° C. for one hour, at which point a solution of (3S-trans)-3-amino-4-methyl-1-(phenylmethoxy)-2-azetidinone, toluenesulfonate (0.95 g) and diisopropylethylamine (0.44 ml) in dimethylformamide (5 ml) is added. The reaction mixture is stirred at room temperature for about 16 hours, then poured into water (100 ml) and extracted with ethyl acetate (three 100 ml portions). The combined organic extracts are washed with water (three 100 ml portions) and aqueous sodium bicarbonate solution (one 100 ml portion), then dried over sodium sulfate and concentrated under reduced pressure to a semi-solid residue. Liquid chromatography (ethyl acetate) affords the desired product as a foam (0.599 g). Recrystallization from chloroform/isopropyl ether yields the title compound, melting point 100°-105° C.

Aufarbeitung

  1. additionis added
  2. extractionextracted with ethyl acetate (three 100 ml portions)
  3. washThe combined organic extracts are washed with water (three 100 ml portions) and aqueous sodium bicarbonate solution (one 100 ml portion)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure to a semi-solid residue

Quellen und Nachweise

ORD-Eintrag
ord-1cd3e7177e15445185e56858cdbd4246
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04533660

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