Diisopropyl Ether → 7beta-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-allyloxyiminoacetamido]-3-[3-amino-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate

HRID 1376418ノート

反応式

HRID 1376418 の反応式
Cl.Cl.Cl.[NH2:4][C@@H:5]1[C:25](=[O:26])[N:7]2[C:8]([C:22]([O-:24])=[O:23])=[C:9]([CH2:12][N+:13]3[N:14]([CH2:19][CH2:20][OH:21])[C:15]([NH2:18])=[CH:16][CH:17]=3)[CH2:10][S:11][C@H:6]12.C[Si](C)(C)NC(=O)C.Cl.[NH2:36][C:37]1[S:41][N:40]=[C:39](/[C:42](=[N:46]/[O:47][CH2:48][CH:49]=[CH2:50])/[C:43](Cl)=[O:44])[N:38]=1.C(OC(C)C)(C)C>O1CCCC1>[NH2:36][C:37]1[S:41][N:40]=[C:39]([C:42](=[N:46][O:47][CH2:48][CH:49]=[CH2:50])[C:43]([NH:4][C@@H:5]2[C:25](=[O:26])[N:7]3[C:8]([C:22]([O-:24])=[O:23])=[C:9]([CH2:12][N+:13]4[N:14]([CH2:19][CH2:20][OH:21])[C:15]([NH2:18])=[CH:16][CH:17]=4)[CH2:10][S:11][C@H:6]23)=[O:44])[N:38]=1

参加物

6

反応物 4

HCID 7914Diisopropyl EtherHCID 25989Acetamide, N-(trimethylsilyl)-HCID 20075415(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-prop-2-enoxyiminoacetyl chloride;hydrochlorideHCID 1317165287beta-Amino-3-[3-amino-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate trihydrochloride

生成物 1

HCID 1317179017beta-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-allyloxyiminoacetamido]-3-[3-amino-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate収率 43.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 7β-amino-3-[3-amino-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate trihydrochloride (2 g) and N-(trimethylsilyl)acetamide (5.85 g) in tetrahydrofuran (40 ml)was added (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-allyloxyiminoacetyl chloride hydrochloride (1.26 g) under ice-cooling. After being stirred for 1 hour at the same temperature, the reaction mixture was poured into diisopropyl ether (200 ml). The resulting precipitate was collected by filtration, dissolved in water (100 ml) and adjusted to pH 2.0 with 5% sodium bicarbonate solution. This solution was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (Trademark: prepared by Mitsubishi Chemical Industries). The desired compound was eluted with 10% isopropyl alcohol and lyophilized to give 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-allyloxyiminoacetamido]-3-[3-amino-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate (syn isomer) (1.07 g).

後処理

  1. temperaturecooling
  2. filtrationThe resulting precipitate was collected by filtration
  3. dissolutiondissolved in water (100 ml)
  4. custom" (Trademark: prepared by Mitsubishi Chemical Industries)
  5. washThe desired compound was eluted with 10% isopropyl alcohol

出典と根拠

ORDレコード
ord-d64a8f4a4efb4e239a1fe2a888924ce5
出典データセット
uspto-grants-1997_09
特許番号
US05663163

反応ノート

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