Methanesulfonyl chloride → HCID 178480383, compound

HRID 1614079Notes

Reaction equation

HRID 1614079 reaction equation
CS(Cl)(=O)=O.[NH2:6][C:7]1[S:8][CH:9]=[C:10]([C:12](=[N:16][O:17][CH:18]2[CH2:21][S:20][CH2:19]2)[C:13]([OH:15])=O)[N:11]=1.C(N(C(C)C)CC)(C)C.[NH2:31][C@@H:32]1[C:49](=[O:50])[N:34]2[C:35]([C:46]([O-:48])=[O:47])=[C:36]([CH2:39][N+:40]3[N:41]([CH3:45])[CH:42]=[CH:43][CH:44]=3)[CH2:37][S:38][C@H:33]12.C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C>CN(C)C=O.O1CCCC1.C(OCC)C>[NH2:6][C:7]1[S:8][CH:9]=[C:10]([C:12](=[N:16][O:17][CH:18]2[CH2:21][S:20][CH2:19]2)[C:13]([NH:31][C@@H:32]2[C:49](=[O:50])[N:34]3[C:35]([C:46]([O-:48])=[O:47])=[C:36]([CH2:39][N+:40]4[N:41]([CH3:45])[CH:42]=[CH:43][CH:44]=4)[CH2:37][S:38][C@H:33]23)=[O:15])[N:11]=1

Participants

9

Reactant 5

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 543232982-(2-Aminothiazol-4-yl)-2-(3-thietanyloxyimino)acetic acidHCID 178480378HCID 178480378, compound

Product 1

HCID 178480383HCID 178480383, compoundYield 24.5%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (0.61 ml) was added to a solution of 2-(2-aminothiazol-4-yl)-2-(3-thietanyloxyimino)acetic acid (syn isomer, 0.99 g) and N,N-diisopropyl-N-ethylamine (1.33 ml) in N,N-dimethylformamide (20 ml) at -55° to -50° C., and the mixture was stirred for 10 minutes to produce an activated acid solution. To a solution of bis(trisfluoroacetic acid) salts of 7β-amino-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (2 g) and N,O-bis(trimethylsilyl)acetamide (3.79 ml) in tetrahydrofuran (20 ml) was added the above activated acid solution under ice-cooling, and the reaction mixture was stirred at the same temperature for an hour. The resultant mixture was poured into diethyl ether, and the precipitates were collected by filtration. The precipitates were suspended in water (20 ml), and the suspension was adjusted to pH 5 with 5% aqueous solution of sodium bicarbonate and subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (Trademark, manufactured by Mitsubishi Chemical Industries) and eluted with 10% aqueous solution of isopropyl alcohol. The fractions containing the object compound were collected, evaporated in vacuo to remove isopropyl alcohol, and lyophilized to give 7β-[2-(2-aminothiazol-4-yl)-2-(3-thietanyloxyimino)acetamido]-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (syn isomer, 0.5 g).

Workup

  1. customto produce an activated acid solution
  2. temperaturecooling
  3. stirringthe reaction mixture was stirred at the same temperature for an hour
  4. filtrationthe precipitates were collected by filtration
  5. wash" (Trademark, manufactured by Mitsubishi Chemical Industries) and eluted with 10% aqueous solution of isopropyl alcohol
  6. additionThe fractions containing the object compound
  7. customwere collected
  8. customevaporated in vacuo
  9. customto remove isopropyl alcohol

Sources & evidence

ORD record
ord-4c27ef5de5c3487e9491ac4c345723dc
Source dataset
uspto-grants-1993_03
Patent number
US05194432

Reaction notes

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