Chlorotrimethylsilane → HCID 178431922, compound

HRID 1764390Notes

Reaction equation

HRID 1764390 reaction equation
[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.[CH2:17]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])C.Cl[Si](C)(C)C.N1CCCC[CH2:31][CH2:30]1>ClCCl>[N:19]1([CH:17]=[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)[CH2:22][CH2:23][CH2:31][CH2:30][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8119AzepaneHCID 8471TriethylamineHCID 178431949HCID 178431949, compound

Product 1

HCID 178431922HCID 178431922, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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, 2H, 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 (0.2M NaOAc:acetone; 1:6) showed a single spot (Rf 0.23).

Workup

  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

Sources & evidence

ORD record
ord-6e61ddd208114329a1a89be7d6d4b1f3
Source dataset
uspto-grants-1978_09
Patent number
US04115385

Reaction notes

Loading…