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Sodium Chloride → 7beta-Phenoxyacetamido-3-methoxy-ceph-2-em-4alpha-carboxylic acid

HRID 127453
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 127453
[N+](C1C=CC(C[O:9][C:10]([C@@H:12]2[N:17]3[C:18](=[O:31])[C@@H:19]([NH:20][C:21](=[O:30])[CH2:22][O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C@H:16]3[S:15][CH:14]=[C:13]2[O:32][CH3:33])=[O:11])=CC=1)([O-])=O.[N+](C1C=CC(COC(C2N3C(=O)[C@@H](NC(=O)COC4C=CC=CC=4)[C@H]3SCC=2OC)=O)=CC=1)([O-])=O.[OH-].[K+].[Cl-].[Na+]>O1CCCC1.C(Cl)Cl>[O:23]([CH2:22][C:21]([NH:20][C@@H:19]1[C:18](=[O:31])[N:17]2[C@@H:12]([C:10]([OH:11])=[O:9])[C:13]([O:32][CH3:33])=[CH:14][S:15][C@H:16]12)=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 12784140HCID 12784140, VerbindungHCID 70559733HCID 70559733, Verbindung

Produkt 1

HCID 128054427beta-Phenoxyacetamido-3-methoxy-ceph-2-em-4alpha-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution prepared at 0° C., of 555 mg (1.11 mmols) of a crude mixture consisting of 7β-phenoxyacetamido-3-methoxy-ceph-2-em-4α-carboxylic acid p-nitrobenzyl ester and 7β-phenoxyacetamido-3-methoxy-ceph-3-em-4-carboxylic acid p-nitrobenzyl ester in the ratio of about 3:1, in 33 ml of tetrahydrofurane, is mixed, whilst stirring, with 16 ml of an 0.1 N potassium hydroxide solution which has been precooled to 0° C. The mixture is stirred for a further 5 minutes at 0° C., 100 ml of ice water and 100 ml of precooled methylene chloride are then added and the whole is stirred up briefly. Addition of 1 ml of saturated aqueous sodium chloride solution causes the two phases to separate. The organic phase is separated off, and the aqueous phase is again washed with 20 ml of methylene chloride, then covered with 50 ml of methylene chloride and acidified with 20 ml of 2 N hydrochloric acid. After shaking up, the organic phase is separated off and the hydrochloric acid solution is extracted twice more with 10 ml of methylene chloride at a time. The combined methylene chloride extracts are dried over sodium sulphate and evaporated in vacuo. The residue is recrystallised from methylene chloride/diethyl ether/pentane and gives 7β-phenoxyacetamido-3-methoxy-ceph-2-em-4α-carboxylic acid of melting point 142°-145° C.

Aufarbeitung

  1. additionis mixed
  2. customhas been precooled to 0° C
  3. stirringthe whole is stirred up briefly
  4. customto separate
  5. customThe organic phase is separated off
  6. washthe aqueous phase is again washed with 20 ml of methylene chloride
  7. stirringAfter shaking up
  8. customthe organic phase is separated off
  9. extractionthe hydrochloric acid solution is extracted twice more with 10 ml of methylene chloride at a time
  10. dry with materialThe combined methylene chloride extracts are dried over sodium sulphate
  11. customevaporated in vacuo
  12. customThe residue is recrystallised from methylene chloride/diethyl ether/pentane

Quellen und Nachweise

ORD-Eintrag
ord-c9b09ef7f4254e85879e921890e9aff6
Quelldatensatz
uspto-grants-1981_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04255328

Notizen zur Reaktion

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