Pyridine → HCID 131710125, Verbindung

HRID 1604921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1604921
[OH:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C:25](=[O:36])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].N1C=CC=CC=1.[CH:43](F)=[O:44]>O1CCCC1>[CH:43]([O:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C:25](=[O:36])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10])=[O:44]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 15153Formyl fluoride2×HCID 390251HCID 390251, Verbindung

Produkt 1

HCID 131710125HCID 131710125, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Diphenylmethyl 3-hydroxymethyl-7β-(2'-thienylacetamido)-ceph-3-em-4-carboxylate (3 g., 5.8 mmole.) and pyridine (6.5 ml., 82 mmole.) were dissolved in dry tetrahydrofuran (100 ml.), and cooled to -60°. A solution of formyl fluoride (~80 mmole.) in dry tetrahydrofuran (100 ml.), and cooled to -60°. A solution of formyl fluoride ( 80 mmole.) in dry tetrahydrofuran was added dropwise and the mixture maintained at -40° for 1 hour. On reaching room temperature, the mixture was filtered, concentrated, and partitioned between ethyl acetate and 2N-hydrochloric acid. On washing with more acid the ethyl acetate solution precipitated some product (1.77 g.); the remaining ethyl acetate was dried and evaporated to give more product (1.32 g.). A sample of the product was recrystallised from ethyl acetate, m.p. 189°, νmax (CHBr3), 1792 (β-lactam), 1730 and 1232 (COOR), 1690 and 1518 cm-1 (CONH). N.M.R. spectrum (dimethylsulphoxide) CHO at 179τ. (Found: C, 61.7; H, 4.4; N, 4.8. C28H24H2O6S2 requires C, 61.3; H, 4.4; N, 5.1%) NF = 0.7 (Kieselgel G plate, benzene:ethyl acetate = 2:1).

Aufarbeitung

  1. temperaturecooled to -60°
  2. temperaturethe mixture maintained at -40° for 1 hour
  3. customOn reaching room temperature
  4. filtrationthe mixture was filtered
  5. concentrationconcentrated
  6. custompartitioned between ethyl acetate and 2N-hydrochloric acid
  7. washOn washing with more acid the ethyl acetate solution
  8. customprecipitated some product (1.77 g.)
  9. dry with materialthe remaining ethyl acetate was dried
  10. customevaporated
  11. customto give more product (1.32 g.)
  12. customA sample of the product was recrystallised from ethyl acetate, m.p. 189°, νmax (CHBr3), 1792 (β-lactam), 1730 and 1232 (COOR), 1690 and 1518 cm-1 (CONH)

Quellen und Nachweise

ORD-Eintrag
ord-86eae3622b1f473fac288fe232338fcb
Quelldatensatz
uspto-grants-1976_04
Patentnummer
US03948906

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