Potassium Carbonate → HCID 88258899, Verbindung

HRID 1421813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1421813
[C:1]([O:4][CH:5](Br)[CH3:6])(=[O:3])[CH3:2].[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:35]/[O:36][CH3:37])/[C:15]([NH:17][C@@H:18]2[C:33](=[O:34])[N:20]3[C:21]([C:30]([O-:32])=[O:31])=[C:22]([C@@H:25]4[CH2:29][CH2:28][CH2:27][O:26]4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1.[Na+].C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.C(OCC)(=O)C>[NH2:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:35]/[O:36][CH3:37])/[C:15]([NH:17][C@@H:18]2[C:33](=[O:34])[N:20]3[C:21]([C:30]([O:32][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH3:6])=[O:31])=[C:22]([C@@H:25]4[CH2:29][CH2:28][CH2:27][O:26]4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 111375051-Bromoethyl acetateHCID 23690298Cefovecin sodium

Produkt 1

HCID 88258899HCID 88258899, VerbindungAusbeute 79,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel2×

Versuchsvorschrift

A solution of (RS)-1-acetoxyethylbromide (267 mg) in 1-methyl-2-pyrrolidinone (2 ml) was added dropwise, over 1 hour, to an ice cold mixture of sodium (6R,7R)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-3-[(S)-tetrahydrofuran-2-yl]ceph-3-em-4-carboxylate (190 mg) and potassium carbonate (110 mg) in 1-methyl-2-pyrrolidinone (1 ml). After 15 minutes the mixture was diluted with ethyl acetate, washed with water, brine, dried (MgSO4), concentrated and flash chromatographed on silica gel eluting with 50,70,80 and 90% ethyl acetate in hexane to give the title compound (172 mg); νmax (CHCl3) 3019, 2929, 1786, 1683, 1520, 13176 and 1135 cm-1 ; δH (CDCl3, 250 MHz) 1.45-1.75 (4H,m), 1.90-2.10 (2H,m), 2.09 and 2.10 (together 3H, 2s), 2.30-2.50 (1H,m), 3.36 and 3.65 (2H, ABq, J 18.8 Hz), 4.93-5.10 (2H,m), 5.90-6.05 (1H,m), 6.94 and 7.07 (together 1H,q,J 5.8 Hz), 7.10 and 7.15 (together 1H, 2s) and 7.60 and 7.67 (together 1H,2d, J 7.4 Hz); [Mass spectrum: +ve ion (3-nitrobenzyl alcohol, sodium acetate) MNa+ (562)].

Aufarbeitung

  1. washwashed with water, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customflash chromatographed on silica gel eluting with 50,70,80 and 90% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-951c75de1b0f44be94d8d794f03f949d
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06077952

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