Ethyl Acetate → HCID 178418679、化合物

HRID 1609672

反応式

HRID 1609672 の反応式
[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

参加物

6

反応物 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、化合物

生成物 1

HCID 178418679HCID 178418679、化合物収率 34.2%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-5c12a75cadde4c6695a76e3a616911db
出典データセット
uspto-grants-1995_03
特許番号
US05401734

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