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Acetic Acid → 7-[2-(2-Formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

HRID 364551
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 364551
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:35][O:36][CH3:37])[C:10]([NH:12][CH:13]2[C:33](=[O:34])[N:15]3[C:16]([C:20]([O:22]CC4C=CC([N+]([O-])=O)=CC=4)=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2].C(O)(=O)C.O.[H][H]>[C].[Pd].O1CCCC1.CO>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:35][O:36][CH3:37])[C:10]([NH:12][CH:13]2[C:33](=[O:34])[N:15]3[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 962WaterHCID 1317124414-Nitrobenzyl 7-[2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 1317124427-[2-(2-Formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acidAusbeute 79,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A suspension of 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (anti isomer, 4.2 g.), 10% palladium carbon (1.7 g.), acetic acid (0.63 ml.), water (6.3 ml.), methanol (42 ml.), and tetrahydrofuran (84 ml.) was subjected to catalytic reduction in a hydrogen atmosphere at room temperature for 2 hours. After removing the catalyst by filtration, the filtrate was concentrated to a volume of about 15 ml. under reduced pressure. Water (30 ml.) and ethyl acetate (50 ml.) were added to the concentrated solution, and the solution was adjusted to pH 8.0 with sodium bicarbonate under stirring. The insoluble substance was removed by filtration, and the aqueous layer was separated and washed with ethyl acetate (50 ml.). The solution was treated, with activated charcoal, and adjusted to pH 2.2 with 10% hydrochloric acid under ice cooling. The precipitates were collected by filtration and washed with water to give 7-[2-(2 -formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (anti isomer, 2.52 g.).

Aufarbeitung

  1. customAfter removing the catalyst
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated to a volume of about 15 ml
  4. additionWater (30 ml.) and ethyl acetate (50 ml.) were added to the concentrated solution
  5. customThe insoluble substance was removed by filtration
  6. customthe aqueous layer was separated
  7. washwashed with ethyl acetate (50 ml.)
  8. additionThe solution was treated, with activated charcoal
  9. filtrationThe precipitates were collected by filtration
  10. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-8327d82dd980422d88f58e6cf3715ee2
Quelldatensatz
uspto-grants-1986_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04604456

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