Hydrochloric Acid → HCID 178460821, Verbindung

HRID 372607Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 372607
Br[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].C([N:39]1[C:43](=[S:44])[NH:42][N:41]=[N:40]1)C.[CH2:45](N(CC)CC)[CH3:46].Cl>O1CCCC1.[Cl-].[Na+].O.C(OCC)(=O)C.O>[CH2:45]([CH:2]([S:44][C:43]1[NH:42][N:41]=[N:40][N:39]=1)[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])[CH3:46]

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 70592080HCID 70592080, VerbindungHCID 178463196HCID 178463196, Verbindung

Produkt 1

HCID 178460821HCID 178460821, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A solution of diphenylmethyl 3-bromomethyl-7β-(2-thienylacetamido)-ceph-3-em-4-carboxylate (11.67 g) and 1-ethyltetrazoline-5-thione (2.6 g) in dry tetrahydrofuran (150 ml) was stirred at 0° and a solution of triethylamine (2.8 ml) in tetrahydrofuran (25 ml) was added, dropwise, over 5 minutes. The resulting suspension was stirred for a further 25 minutes, during which time the temperature was allowed to rise to ca. 20°, and was then added, over 5 minutes, to a stirred mixture of 2N-hydrochloric acid (50 ml), water (350 ml), brine (350 ml), and ethyl acetate (600 ml). The organic phase was separated, and washed with 2N-hydrochloric acid, saturated sodium bicarbonate, water, and brine, and dried and evaporated to a foam (11.71 g). A solution of this foam in benzene (25 ml) was purified by chromatography on kieselgel (200 g), with benzene:ethyl acetate = 5:1 as eluant. Appropriate fractions were combined and the solvents evaporated in vacuo. The residue was dissolved in methylene dichloride, and the solution run into petroleum ether to give the ester as a pale-yellow, amorphous solid (8.585g, 68%); [α]D23 - 131° (c 0.97. CHCl3); λmax. (EtOH) 264 nm (ε 7,300), τ (CDCl3) values include 4.12 (7-H, dd, J 5 and 9 Hz.), 5.04 (6-H, d, J 5 Hz.), 5.83 (CH3CH2 --, q, J 7 Hz.), and 8.57 (CH3CH2 --, t, J 7 Hz.).

Aufarbeitung

  1. customto rise to ca. 20°
  2. customThe organic phase was separated
  3. washwashed with 2N-hydrochloric acid, saturated sodium bicarbonate, water, and brine
  4. customdried
  5. customevaporated to a foam (11.71 g)
  6. customA solution of this foam in benzene (25 ml) was purified by chromatography on kieselgel (200 g), with benzene
  7. customthe solvents evaporated in vacuo
  8. dissolutionThe residue was dissolved in methylene dichloride

Quellen und Nachweise

ORD-Eintrag
ord-b5dc3611adfd40d4ae3668cfb71f7431
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04091209

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