Chloroform → benzhydryl 7-[2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-[(Z)-2-(2-pyridyl)vinylthio]-3-cephem-4-carboxylate

HRID 704267ノート

反応式

HRID 704267 の反応式
[NH2:1][CH:2]1[C:34](=[O:35])[N:4]2[C:5]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:6]([S:9]/[CH:10]=[CH:11]\[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[CH2:7][S:8][C@H:3]12.C[Si](NC(=O)N[Si](C)(C)C)(C)C.Cl.[CH2:49]([O:52][N:53]=[C:54]([C:58]1[N:62]=[C:61]([NH2:63])[S:60][N:59]=1)[C:55](Cl)=[O:56])[CH:50]=[CH2:51].C(Cl)(Cl)Cl>C(Cl)Cl.O1CCCC1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+].O>[CH2:49]([O:52][N:53]=[C:54]([C:58]1[N:62]=[C:61]([NH2:63])[S:60][N:59]=1)[C:55]([NH:1][CH:2]1[C:34](=[O:35])[N:4]2[C:5]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:19])=[C:6]([S:9]/[CH:10]=[CH:11]\[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[CH2:7][S:8][C@H:3]12)=[O:56])[CH:50]=[CH2:51]

参加物

10

反応物 4

HCID 6212ChloroformHCID 875621,3-Bis(trimethylsilyl)ureaHCID 67948085benzhydryl 7-amino-3-[(Z)-2-(2-pyridyl)vinylthio]-3-cephem-4-carboxylateHCID 736584962-Allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetyl chloride hydrochloride

生成物 1

HCID 131716151benzhydryl 7-[2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-[(Z)-2-(2-pyridyl)vinylthio]-3-cephem-4-carboxylate

試薬・触媒・溶媒 5

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

A mixture of benzhydryl 7-amino-3-[(Z)-2-(2-pyridyl)vinylthio]-3-cephem-4-carboxylate (600 ml) and bis(trimethylsilyl)urea (981 mg) in methylene chloride (6 ml) was stirred at 30°~35° C. for 30 minutes to give a clear solution. To the clear solution was added 2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetyl chloride monohydrochloride (syn isomer) (480 mg) at 20° C. and the mixture was stirred for 30 minutes at -10°~-15° C. The mixture was poured into a mixture of chloroform and water. The organic layer was separated and concentrated in vacuo to give a residue. The residue was dissolved in a mixture of tetrahydrofuran, ethyl acetate and dilute aqueous solution of sodium bicarbonate. The organic layer was separated, washed with dilute aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate and concentrated in vacuo, and the residue was triturated with diisopropyl ether to give benzhydryl 7-[2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-[(Z)-2-(2-pyridyl)vinylthio]-3-cephem-4-carboxylate (syn isomer) (848 mg).

後処理

  1. customto give a clear solution
  2. stirringthe mixture was stirred for 30 minutes at -10°~-15° C
  3. customThe organic layer was separated
  4. concentrationconcentrated in vacuo
  5. customto give a residue
  6. customThe organic layer was separated
  7. washwashed with dilute aqueous solution of sodium bicarbonate
  8. dry with materiala saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customthe residue was triturated with diisopropyl ether

出典と根拠

ORDレコード
ord-5fe170c5074a4935ba37d8ce4b969c32
出典データセット
uspto-grants-1991_01
特許番号
US04985555

反応ノート

読み込み中…