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m-Chloroperbenzoic acid → Diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate 1-oxide

HRID 596835
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 596835
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:39](=[O:40])[N:12]2[CH:13]([C:23]([O:25][CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[C:14]([CH:17]([O:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:15][S:16][C@H:11]12)=[O:8].ClC1C=CC=C(C(OO)=[O:49])C=1>C(Cl)(Cl)Cl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:39](=[O:40])[N:12]2[C:13]([C:23]([O:25][CH:26]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:24])=[C:14]([CH:17]([O:19][C:20](=[O:22])[CH3:21])[CH3:18])[CH2:15][S:16](=[O:49])[C@H:11]12)=[O:8]
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Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 70617660Benzhydryl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-2-cephem-4-carboxylate

Produkt 1

HCID 70617865Diphenylmethyl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-3-cephem-4-carboxylate 1-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel3×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a cooled (5° C.), stirred solution of 0.897 g. of benzhydryl 7-(2-thienylacetamido)-3-(1-acetoxyethyl)-2-cephem-4-carboxylate in 80 ml. of chloroform was added a solution of 0.348 g. of 85 percent m-chloroperbenzoic acid in 3 ml. of chloroform. The reaction mixture was allowed to stir with cooling for 30 minutes after which time it was transferred to a separatory funnel with the aid of additional chloroform and washed successively with sodium bicarbonate solution (2X), and brine (2X) and dried over anhydrous sodium sulfate. The residue obtained by evaporation in vacuo to a froth which was chromatographed on a silica gel column using a toluene-ethyl acetate gradient to give 0.243 g. (26 percent) of what was labeled diastereoisomer I and 0.514 g. (55 percent) of what was labeled diastereoisomer II of the title product; isomer I coming off the column first.

Aufarbeitung

  1. stirringto stir
  2. temperaturewith cooling for 30 minutes after which time it
  3. washwashed successively with sodium bicarbonate solution (2X), and brine (2X)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue obtained by evaporation in vacuo to a froth which
  6. customwas chromatographed on a silica gel column
  7. customto give 0.243 g

Quellen und Nachweise

ORD-Eintrag
ord-b2bde4495ffd467b9facc12c7713924b
Quelldatensatz
uspto-grants-1977_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04012380

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