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 2351137노트

반응식

HRID 2351137 반응식
[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(N[Si](C)(C)C)=O)(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]

참가 물질

10

반응물 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

생성물 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

시약·촉매·용매 5

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

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-3yl) 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).

후처리

  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

출처 및 근거

ORD 기록
ord-389852be3e65462f9828cf9c35d6ffc4
출처 데이터셋
uspto-grants-1989_10
특허 번호
US04871730

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