Triethylamine → p-Nitrobenzyl 3-chloro-7-(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopent-1-yl)-3-cephem-4-carboxylate

HRID 235608Notes

Reaction equation

HRID 235608 reaction equation
Cl[Si:2]([CH3:10])([CH3:9])[CH2:3][CH2:4][Si:5](Cl)([CH3:7])[CH3:6].[NH2:11][CH:12]1[C:33](=[O:34])[N:14]2[C:15]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=3)=[O:21])=[C:16]([Cl:19])[CH2:17][S:18][C@H:13]12.C(N(CC)CC)C>C(Cl)Cl>[Cl:19][C:16]1[CH2:17][S:18][C@@H:13]2[CH:12]([N:11]3[Si:5]([CH3:7])([CH3:6])[CH2:4][CH2:3][Si:2]3([CH3:10])[CH3:9])[C:33](=[O:34])[N:14]2[C:15]=1[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 835521,2-Bis(chlorodimethylsilyl)ethaneHCID 676435564-Nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate

Product 1

HCID 70431224p-Nitrobenzyl 3-chloro-7-(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopent-1-yl)-3-cephem-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1,2-bis(chlorodimethylsilyl)ethane (3.2 g) in methylene chloride (20 ml) was added to a stirred mixture of p-nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate (5.0 g) and triethylamine (4.9 ml) in methylene chloride (25 ml) under a nitrogen atmosphere. The mixture was stirred at reflux for 16 hours, then allowed to cool to room temperature, and washed with 8% aqueous sodium hydrogen phosphate solution. The organic layer was separated, dried with magnesium sulphate, and evaporated under reduced pressure to give the title compound as a gum, nmr (CDCl3) δ0.17 (s, 12H), 0.78 (s, 4H), 3.38+3.82 (ABq, J=18 Hz, 2H), 4.76 (d, J=4 Hz, 1H), 4.93 (d, J=4 Hz, 1H), 5.28 (s, 2H), 7.3-8.1 (m, 4H).

Workup

  1. temperatureat reflux for 16 hours
  2. washwashed with 8% aqueous sodium hydrogen phosphate solution
  3. customThe organic layer was separated
  4. dry with materialdried with magnesium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c910ce8d92534fcf9c820cf4cb5b1971
Source dataset
uspto-grants-1987_02
Patent number
US04640798

Reaction notes

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