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Diisopropyl Ether → Cefditoren Pivoxil

HRID 2373532
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HRID 2373532 반응식
[CH3:1][C:2]1[N:6]=[CH:5][S:4][C:3]=1/[CH:7]=[CH:8]\[C:9]1[CH2:30][S:29][C@@H:12]2[C@H:13]([NH:16][C:17](/[C:19](/[C:23]3[N:27]=[C:26]([NH2:28])[S:25][CH:24]=3)=[N:20]\[O:21][CH3:22])=[O:18])[C:14](=[O:15])[N:11]2[C:10]=1[C:31]([O-:33])=[O:32].[Na+].C(=O)(O)[O-].[Na+].[C:40]([O:46][CH2:47]I)(=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42].C(OC(C)C)(C)C>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.CN(C=O)C>[CH3:1][C:2]1[N:6]=[CH:5][S:4][C:3]=1/[CH:7]=[CH:8]\[C:9]1[CH2:30][S:29][C@@H:12]2[C@H:13]([NH:16][C:17](/[C:19](/[C:23]3[N:27]=[C:26]([NH2:28])[S:25][CH:24]=3)=[N:20]\[O:21][CH3:22])=[O:18])[C:14](=[O:15])[N:11]2[C:10]=1[C:31]([O:33][CH2:47][O:46][C:40]([C:41]([CH3:44])([CH3:43])[CH3:42])=[O:45])=[O:32]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 7914Diisopropyl EtherHCID 104401Iodomethyl pivalateHCID 516892Sodium BicarbonateHCID 236730425-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-3-[(1Z)-2-(4-methyl-5-thiazolyl)ethenyl]-8-oxo-, sodium salt (1:1), (6R,7R)-

생성물 1

HCID 6437877Cefditoren Pivoxil
수율 97%

시약·촉매·용매 3

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
-20 °C

실험 절차

To DMF (80 ml), Cefditoren Sodium (10 gm) was added at 30° C. and stirred to get a clear solution. To the clear solution, solid sodium bicarbonate (1.6 gm), and tetra butyl ammonium hydrogen sulphate were added. The reaction mass was cooled to −20° C. and iodomethyl pivalate (9.76 gm) was charged and stirred for 60 minutes. The reaction mass was poured into isopropyl ether (100 ml). To this reaction mixture DM Water (100 ml) was added. The solid obtained was stirred at 5° C., filtered, washed with water and IPE, and finally dried to get the title compound. Purity(HPLC): 97-99% Yield: 8.5 gm.

후처리

  1. customto get a clear solution
  2. stirringstirred for 60 minutes
  3. customThe solid obtained
  4. stirringwas stirred at 5° C.
  5. filtrationfiltered
  6. washwashed with water and IPE
  7. customfinally dried

출처 및 근거

ORD 기록
ord-aaa7e59a933d4814aef17dc9c80dc9f7
출처 데이터셋
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07459550B2

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