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 1376418노트

반응식

HRID 1376418 반응식
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

참가 물질

6

반응물 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

생성물 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-carboxylate수율 43.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d64a8f4a4efb4e239a1fe2a888924ce5
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05663163

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