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Hydrochloric Acid → HCID 70617653, Verbindung

HRID 596831
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 596831
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:35](=[O:36])[N:12]2[CH:13]([C:19]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[C:14]([CH:17]=[O:18])=[CH:15][S:16][C@H:11]12)=[O:8].O1CCC[CH2:38]1.[Br].C[Mg].Cl>C(OCC)C.C(OCC)(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:35](=[O:36])[N:12]2[CH:13]([C:19]([O:21][CH:22]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:20])[C:14]([CH:17]([OH:18])[CH3:38])=[CH:15][S:16][C@H:11]12)=[O:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric Acid2×HCID 8028TetrahydrofuranHCID 88777142HCID 88777142, VerbindungHCID 178419573HCID 178419573, Verbindung

Produkt 1

HCID 70617653HCID 70617653, VerbindungAusbeute 63,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283
Diethyl Ether
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a cooled (-73°), stirred solution of 5.19 g. of benzhydryl 7-(2-thienylacetamido)-3-formyl-2-cephem-4-carboxylate in 60 ml. of tetrahydrofuran under an argon atmosphere was added 10 ml. of a cold (-10°) 3 molar solution of methylmagnesium bromine in ethyl ether. The reaction mixture was stirred with cooling for 4 minutes after which time 10 ml. of 1N.HCl was added. The solution was then allowed to warm to 0° in an ice bath. The reaction mixture was transferred to separatory funnel with the aid of cold ethyl acetate and 1N.HCl. The organic layer was separated and washed with cold 1N.HCl (2X) and brine (2X), and dried over anhydrous sodium sulfate. Evaporation in vacuo to dryness gave a crude product which was chromatographed on silica gel using a toluene-ethyl acetate gradient to give 3.40 g. (63.9 percent) of the title product as a mixture of diastereoisomeric carbinols. Although both isomers have approximately the same rf value, careful fractionation of the column resulted in the isolation of the pure isomers. Isomer I (that which was eluded from the column first) crystallized from methylene chloride/hexane to provide white crystals (m.p. 133.5°-134.5°): ir (CHCl3) 1782 cm-1 (lactam C = O); nmr (CDCl3) δ1.17 (d, 3, J = 6.0 Hz,--CH(OH)CH3), 2.85 (broad s, 1, --OH), 3.79 (s, 2, side chain CH2), 4.27 (m, 1,--CH(OH)CH3), 5.10 (s, 1, C4 --H), 5.13 (d, 1, J = 4.0 Hz, C6 --H), 5.49 (q, 1, J = 4.0 and 8.0 Hz, C7 --H) and 6.31 (s, 1, C2 --H).

Aufarbeitung

  1. temperatureTo a cooled (-73°)
  2. stirringThe reaction mixture was stirred
  3. temperaturewith cooling for 4 minutes after which time 10 ml
  4. temperatureto warm to 0° in an ice bath
  5. customThe organic layer was separated
  6. washwashed with cold 1N
  7. dry with materialHCl (2X) and brine (2X), and dried over anhydrous sodium sulfate
  8. customEvaporation in vacuo to dryness
  9. customgave a crude product which
  10. customwas chromatographed on silica gel using a toluene-ethyl acetate gradient
  11. customto give 3.40 g

Quellen und Nachweise

ORD-Eintrag
ord-7369141216ad464993c8204528874096
Quelldatensatz
uspto-grants-1977_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04012380

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