Pyridine → benzhydryl 7-amino-3-[(Z)-2-(4-methyl-1,2,3-thiadiazol-5-yl)vinyl]-3-cephem-4-carboxylate

HRID 1461170노트

반응식

HRID 1461170 반응식
P(Cl)(Cl)(Cl)(Cl)Cl.N1C=CC=CC=1.C1(CC([NH:22][CH:23]2[C:54](=[O:55])[N:25]3[C:26]([C:38]([O:40][CH:41]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)=[O:39])=[C:27]([CH:30]=[CH:31][C:32]4[S:36][N:35]=[N:34][C:33]=4[CH3:37])[CH2:28][S:29][C@H:24]23)=O)C=CC=CC=1.C(=O)(O)[O-].[Na+]>O.CO.C(Cl)Cl>[NH2:22][CH:23]1[C:54](=[O:55])[N:25]2[C:26]([C:38]([O:40][CH:41]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[O:39])=[C:27](/[CH:30]=[CH:31]\[C:32]3[S:36][N:35]=[N:34][C:33]=3[CH3:37])[CH2:28][S:29][C@H:24]12

참가 물질

8

반응물 4

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 131717108Benzhydryl 7-phenylacetamido-3-[2-(4-methyl-1,2,3-thiadiazol-5-yl)vinyl]-3-cephem-4-carboxylate

생성물 1

HCID 14621702benzhydryl 7-amino-3-[(Z)-2-(4-methyl-1,2,3-thiadiazol-5-yl)vinyl]-3-cephem-4-carboxylate수율 45%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

Phosphorus pentachloride (5.83 g, 28 mmol) was made a methylene chloride (50 ml) suspension, pyridine (7.39 g, 93 mmol) was added at 5°-10° C. and stirring was continued for 40 minutes. Added all at once at 5° C. thereto was benzhydryl 7-phenylacetamido-3-[2-(4-methyl-1,2,3-thiadiazol-5-yl)vinyl]-3-cephem-4-carboxylate (E/Z=1/3.5, 5.69 g, 9.36 mmol), and the mixture was stirred at the same temperature for 3 hours. Methanol (38 ml) was slowly added to the reaction mixture at -50° C., and it was stirred for 1 hour at -50° to -30° C. Water (7 ml) was added at -10° C. and the reaction temperature was set at 0° C. and then it was stirred for 10 minutes. The reaction solution was adjusted to pH 6 with saturated sodium bicarbonate solution and then extracted with methylene chloride. It was washed with water and then the methylene chloride layer was dried over magnesium sulfate. The solvent was distilled off and then ethyl acetate was added to the residue. Precipitates were filtered and then cleansed with ethyl acetate thereby benzhydryl 7-amino-3-[(Z)-2-(4-methyl-1,2,3-thiadiazol-5-yl)vinyl]-3-cephem-4-carboxylate (2.06 g, 45% yield) was obtained.

후처리

  1. additionwas added at 5°-10° C.
  2. additionAdded all at once at 5° C.
  3. stirringthe mixture was stirred at the same temperature for 3 hours
  4. stirringit was stirred for 1 hour at -50° to -30° C
  5. customwas set at 0° C.
  6. stirringit was stirred for 10 minutes
  7. extractionextracted with methylene chloride
  8. washIt was washed with water
  9. dry with materialthe methylene chloride layer was dried over magnesium sulfate
  10. distillationThe solvent was distilled off
  11. additionethyl acetate was added to the residue
  12. customPrecipitates
  13. filtrationwere filtered

출처 및 근거

ORD 기록
ord-0cdb750bb18843eb9c78b670013814ba
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05073551

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