Ethyl Acetate → HCID 178418679, compound

HRID 1609672

Reaction equation

HRID 1609672 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:15]=[C:14]([OH:16])[C:13]([OH:17])=[CH:12][N:11]=2)=[O:9])[CH2:4][CH2:3]1.C(C(CCCC)C([O-])=O)C.[Na+].FC(F)(F)C(O)=O.[NH2:36][C:37]1[S:41][N:40]=[C:39]([C:42](=[N:60][O:61][CH2:62][CH:63]=[CH2:64])[C:43]([NH:45][C@@H:46]2[C:58](=[O:59])[N:48]3[C:49]([C:55]([OH:57])=[O:56])=[C:50]([CH2:53]Cl)[CH2:51][S:52][C@H:47]23)=[O:44])[N:38]=1.C(OCC)(=O)C>CS(C)=O>[NH2:36][C:37]1[S:41][N:40]=[C:39]([C:42](=[N:60][O:61][CH2:62][CH:63]=[CH2:64])[C:43]([NH:45][C@@H:46]2[C:58](=[O:59])[N:48]3[C:49]([C:55]([O-:57])=[O:56])=[C:50]([CH2:53][N+:2]4([CH3:1])[CH2:7][CH2:6][N:5]([C:8]([C:10]5[CH:15]=[C:14]([OH:16])[C:13]([OH:17])=[CH:12][N:11]=5)=[O:9])[CH2:4][CH2:3]4)[CH2:51][S:52][C@H:47]23)=[O:44])[N:38]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 23672331Sodium 2-ethylhexanoateHCID 1317181447beta-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-allyloxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate trifluoroacetateHCID 178418632HCID 178418632, compound

Product 1

HCID 178418679HCID 178418679, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a suspension of 1-methyl-4-(4,5-dihydroxy-2-pyridylcarbonyl)piperazine (800 mg) in dimethyl sulfoxide (8 ml) was added sodium 2-ethylhexanoate (840 mg). The solution was added dropwise to a solution of 7β-[2-(5-amino-1,2,4-thiadiazol- 3-yl) -2-allyloxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate trifluoroacetate (syn isomer) (965 mg) in dimethyl sulfoxide (7 ml) at room temperature. After being stirred for 4 hours, the mixture was poured into ethyl acetate (200 ml) and the resulting precipitates were collected by filtration. The precipitates were dissolved in water and then adjusted to pH 3.0 with aqueous sodium bicarbonate. The resulting solution was subjected to column chromatography on Diaion HP-20 using 15% aqueous isopropyl alcohol as an eluent and the objective fraction was lyophilized to give 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-allyloxyiminoacetamido]-3-[1-methyl-4-(4,5-dihydroxy-2-pyridylcarbonyl)-1-piperazinio]methyl-3-cephem-4-carboxylate (syn isomer) (380 mg).

Workup

  1. customthe resulting precipitates
  2. filtrationwere collected by filtration
  3. dissolutionThe precipitates were dissolved in water

Sources & evidence

ORD record
ord-5c12a75cadde4c6695a76e3a616911db
Source dataset
uspto-grants-1995_03
Patent number
US05401734

Linked notes

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