Water → 3-Methyl-7-[2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)acetamido]ceph-3-em-4-carboxylic acid

HRID 1702734

Reaktionsgleichung

Reaktionsgleichung von HRID 1702734
[CH3:1][C:2]1[CH2:21][S:20][C@@H:5]2[C@H:6]([NH:9][C:10]([C@H:12]([NH2:19])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[O:11])[C:7](=[O:8])[N:4]2[C:3]=1[C:22]([OH:24])=[O:23].O.C(=O)([O-])[O-].[K+].[K+].[CH2:32]([N:34]1[CH2:39][CH2:38][N:37]([C:40](Cl)=[O:41])[C:36](=[O:43])[C:35]1=[O:44])[CH3:33]>C(OCC)(=O)C>[CH3:1][C:2]1[CH2:21][S:20][C@@H:5]2[CH:6]([NH:9][C:10](=[O:11])[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:19][C:40]([N:37]3[CH2:38][CH2:39][N:34]([CH2:32][CH3:33])[C:35](=[O:44])[C:36]3=[O:43])=[O:41])[C:7](=[O:8])[N:4]2[C:3]=1[C:22]([OH:24])=[O:23]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27447CephalexinHCID 1088134-Ethyl-2,3-dioxopiperazinecarbonyl chloride

Produkt 1

HCID 705073103-Methyl-7-[2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)acetamido]ceph-3-em-4-carboxylic acidAusbeute 55,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

Cephalexin (696 mg., 2 mmoles) was dissolved in 10 ml. of water at 5° C. by the action of potassium carbonate (304 mg., 2.2 mmoles). Ethyl acetate (5 ml.) was added and then 4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride (450 mg., 2.2 mole) was added over a period of 15 minutes at 0°-5° C. After addition was complete, the reaction mixture was stirred for an additional 30 minutes, at which time the ethyl acetate layer was separated and the aqueous phase washed with an additional portion of ethyl acetate. The aqueous phase was adjusted to 2.5 and the product extracted into several portions of fresh ethyl acetate. The acidic ethyl acetate extracts were combined, back-washed with water, washed with brine, dried over anhydrous magnesium sulfate, evaporated to dryness in vacuo, and the residue crystallized from methylene chloride to yield 3-methyl-7-[2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)acetamido]ceph-3-em-4-carboxylic acid (568 mg., m.p. 199°-200° C.).

Aufarbeitung

  1. customat 5° C.
  2. additionAfter addition
  3. customwas separated
  4. washthe aqueous phase washed with an additional portion of ethyl acetate
  5. extractionthe product extracted into several portions of fresh ethyl acetate
  6. washback-washed with water
  7. washwashed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated to dryness in vacuo
  10. customthe residue crystallized from methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-9ef3d93a75ae4a7a987955e3e4350680
Quelldatensatz
uspto-grants-1982_09
Patentnummer
US04348264

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