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Ethyl Acetate → (4-nitrophenyl)methyl (1R,4R,5R,8R)-4-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3,10-dioxo-11-oxa-6-thia-2-azatricyclo[6.3.0.02,5]undecane-1-carboxylate

HRID 329543
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 329543
ClCC([NH:5][C:6]1[S:7][CH:8]=[C:9](/[C:11](=[N:41]/[O:42][CH3:43])/[C:12]([NH:14][C@@H:15]2[C:25](=[O:26])[N:24]3[C@@H:16]2[S:17][CH2:18][C@H:19]2[C@:23]3([C:27]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=3)=[O:28])[O:22][C:21](=[O:40])[CH2:20]2)=[O:13])[N:10]=1)=O.CNC(=S)[S-].[Na+].C(OCC)(=O)C>CN(C)C=O>[NH2:5][C:6]1[S:7][CH:8]=[C:9](/[C:11](=[N:41]/[O:42][CH3:43])/[C:12]([NH:14][C@@H:15]2[C:25](=[O:26])[N:24]3[C@@H:16]2[S:17][CH2:18][C@H:19]2[C@:23]3([C:27]([O:29][CH2:30][C:31]3[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][CH:36]=3)=[O:28])[O:22][C:21](=[O:40])[CH2:20]2)=[O:13])[N:10]=1
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Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 5366415Metam-sodiumHCID 178502836HCID 178502836, Verbindung

Produkt 1

HCID 15117590(4-nitrophenyl)methyl (1R,4R,5R,8R)-4-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3,10-dioxo-11-oxa-6-thia-2-azatricyclo[6.3.0.02,5]undecane-1-carboxylateAusbeute 69,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

In 5 ml of anhydrous N,N-dimethylformamide was dissolved 0.334 g of the compound obtained in Example 16, to which was added 0.132 g of sodium N-methyldithiocarbamate, folowed by stirring at room temperature for 1.5 hour. To the reaction mixture was added 30 ml of ethyl acetate, which was washed with water and then dried (MgSO4). The solvent was distilled off under reduced pressure, and the residue was subjected to a silica gel column chromatography, followed by elution with ethyl acetate-chloroform-methanol (15:15:1). Fractions containing the end product were combined and concentrated under reduced pressure to give 0.206 g of the subject compound as powders.

Aufarbeitung

  1. washwas washed with water
  2. dry with materialdried (MgSO4)
  3. distillationThe solvent was distilled off under reduced pressure
  4. washfollowed by elution with ethyl acetate-chloroform-methanol (15:15:1)
  5. additionFractions containing the end product
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cd22404d0edb43159e4243812c98104b
Quelldatensatz
uspto-grants-1990_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04891427

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