Chlorotrimethylsilane → HCID 178431922, Verbindung

HRID 1448399Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1448399
[NH2:1][CH:2]1[C:15](=[O:16])[N:4]2[CH:5]([C:10]3[NH:14][N:13]=[N:12][N:11]=3)[C:6]([CH3:9])([CH3:8])[S:7][C@H:3]12.C(N(CC)CC)C.Cl[Si](C)(C)C.CO[CH:31](OC)[N:32]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>ClCCl>[N:32]1([CH:31]=[N:1][CH:2]2[C:15](=[O:16])[N:4]3[CH:5]([C:10]4[NH:11][N:12]=[N:13][N:14]=4)[C:6]([CH3:8])([CH3:9])[S:7][C@H:3]23)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Komponenten

6

Edukt 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 1183521-(Dimethoxymethyl)hexahydro-1H-azepineHCID 178431949HCID 178431949, Verbindung

Produkt 1

HCID 178431922HCID 178431922, VerbindungAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 1.2 g (5 mmoles) of 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam, 1.0 g (10 mmole) of triethylamine and 30 ml of dichloromethane, cooled to 0° C., is added 0.54 g (5 mmole) of chlorotrimethylsilane. After 15 minutes, 0.86 (5 mmole) of 1-(dimethoxymethyl)hexahydroazepine (British Pat. No. 1,293,590) is added, and stirring is continued for a further 1 hour. The volatile components are removed by evaporation in vacuo, and then the residue is extracted with 25 ml of acetone. The insoluble material is filtered off, and the acetone is evaporated in vacuo to a yellow foam, which changes to a white powder on trituration with ether. This affords 1.44 g (82% yield) of 6-([hexahydro-1-azepinyl]methyleneamino)-2,2-dimethyl-3-(5-tetrazolyl)penam. The infrared spectrum of the product (KBr disc) shows absorption bands at 1795 cm-1 (β-lactam), 1706 cm-1 and 1645 cm-1. The NMR spectrum (CDCl3) shows absorption bands at 8.00 ppm (singlet, 1H, N--CH=N), 5.90 and 5.60 ppm (two doublets, 2 H, J=4 Hz, C-5 and C-6 hydrogens), 5.40 ppm (singlet, 1H, C-3 hydrogen), 3.90-3.50 (multiplet, 4H, CH2 --N--CH2), 2.00-1.50 ppm (multiplet, 11H, C-2 methyl hydrogens and [CH2 ]4) and 1.20 ppm (singlet, 3H, C-2 methyl hydrogens). Examination of the product by thin-layer chromatography (0.2 M NaOAc: acetone; 1:6) showed a single spot (Rf 0.23).

Aufarbeitung

  1. addition1,293,590) is added
  2. waitis continued for a further 1 hour
  3. customThe volatile components are removed by evaporation in vacuo
  4. extractionthe residue is extracted with 25 ml of acetone
  5. filtrationThe insoluble material is filtered off
  6. customthe acetone is evaporated in vacuo to a yellow foam, which

Quellen und Nachweise

ORD-Eintrag
ord-bce9ff8a00ea48c8bbe419db9b808d35
Quelldatensatz
uspto-grants-1979_12
Patentnummer
US04179511

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