Hydrogen Bromide → t-butyl 3-acetoxymethyl-7-(5-hexahydro-1H-azepin-1-ylmethyleneaminomethylbenzimidazol-2-yl)aminoceph-3-em-4-carboxylate

HRID 1463169Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1463169
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:20]([NH:21][C:22]3[NH:23][C:24]4[CH:30]=[C:29]([CH2:31][NH2:32])[CH:28]=[CH:27][C:25]=4[N:26]=3)[C:19](=[O:33])[N:10]2[C:11]=1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=[O:3])[CH3:2].CO[CH:36](OC)[N:37]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.C(N(CC)CC)C.Br>O1CCOCC1.CO>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:20]([NH:21][C:22]3[NH:23][C:24]4[CH:30]=[C:29]([CH2:31][N:32]=[CH:36][N:37]5[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]5)[CH:28]=[CH:27][C:25]=4[N:26]=3)[C:19](=[O:33])[N:10]2[C:11]=1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 260Hydrogen BromideHCID 8471TriethylamineHCID 1183521-(Dimethoxymethyl)hexahydro-1H-azepineHCID 70509618t-Butyl 3-acetoxymethyl-7-(5-aminomethylbenzimidazol-2-yl)aminoceph-3-em-4-carboxylate

Produkt 1

HCID 70508669t-butyl 3-acetoxymethyl-7-(5-hexahydro-1H-azepin-1-ylmethyleneaminomethylbenzimidazol-2-yl)aminoceph-3-em-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of t-butyl 3-acetoxymethyl-7-(5-aminomethylbenzimidazol-2-yl)aminoceph-3-em-4-carboxylate (93 mg.) in dioxane (2 ml.) and methanol (3 ml.) at 20° was added dimethoxyhexahydro-1H-azepin-1-ylmethane (30 mg.) and then triethylamine. The mixture was cooled to 0° and stirred for 30 minutes. Two equivalents of HBr in methanol were added and the solvent evaporated. The residue was dissolved in the minimum CH2Cl2 and triethylamine hydrobromide precipitated by addition of ether. The product was purified by chromatography on magnesium silicate using CH2Cl2 /MeOH 98:2 v/v as eluant to give t-butyl 3-acetoxymethyl-7-(5-hexahydro-1H-azepin-1-ylmethyleneaminomethylbenzimidazol-2-yl)aminoceph-3-em-4-carboxylate having the following n.m.r. in d6DMSO: 1.63 (s, 9H); 1.7 (s, 8H); 2.17 (s, 3H); 3.3-4.0 (br, 6H); 4.67 (s, 2H); 4.75 (d, 1H); 5.1 (d, 1H); 5.38 (d, 1H); 6.0 (d, 1H); 6.8-7.5 (m, 3H); 8.43 (s, 1H).

Aufarbeitung

  1. temperatureThe mixture was cooled to 0°
  2. customthe solvent evaporated
  3. dissolutionThe residue was dissolved in the minimum CH2Cl2 and triethylamine hydrobromide
  4. customprecipitated by addition of ether
  5. customThe product was purified by chromatography on magnesium silicate

Quellen und Nachweise

ORD-Eintrag
ord-368df7cb7eb640e5b92bb7a84167fc7b
Quelldatensatz
uspto-grants-1984_07
Patentnummer
US04463173

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