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Dimethylformamide → 4-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-cyclohexyliminoacetamido]-3-cephem-4-carboxylate

HRID 544020
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HRID 544020 반응식
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13]OC2CCCCC2)[C:10]([OH:12])=O)[N:8]=1)=[O:2].CN(C)C=O.P(Cl)(Cl)(Cl)=O.[NH2:31][CH:32]1[C:52](=[O:53])[N:34]2[C:35]([C:39]([O:41][CH2:42][C:43]3[CH:48]=[CH:47][C:46]([N+:49]([O-:51])=[O:50])=[CH:45][CH:44]=3)=[O:40])=[CH:36][CH2:37][S:38][C@H:33]12>O.CC(C)=O.O1CCCC1>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][CH:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)[C:10]([NH:31][CH:32]2[C:52](=[O:53])[N:34]3[C:35]([C:39]([O:41][CH2:42][C:43]4[CH:44]=[CH:45][C:46]([N+:49]([O-:51])=[O:50])=[CH:47][CH:48]=4)=[O:40])=[CH:36][CH2:37][S:38][C@H:33]23)=[O:12])[N:8]=1)=[O:2]
참가 물질실험 절차출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 12775080p-Nitrobenzyl 7-amino-3-cephem-4-carboxylateHCID 53844359HCID 53844359, 화합물

생성물 1

HCID 887178974-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-cyclohexyliminoacetamido]-3-cephem-4-carboxylate수율 180.3%

시약·촉매·용매 3

HCID 180Acetone용매
HCID 962Water용매
HCID 8028Tetrahydrofuran용매

실험 절차

2-(2-Formamidothiazol-4-yl)-2-cyclohexyloxyiminoacetic acid (syn isomer, 0.9 g.), N,N-dimethylformamide (266 mg.), phosphoryl chloride (557 mg.), tetrahydrofuran (20 ml.), 4-nitrobenzyl 7-amino-3-cephem-4-carboxylate (1.05 g.), acetone (3 ml.) and water (3 ml.) were treated in a similar manner to that of Example 15-(1) to give 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-cyclohexyliminoacetamido]-3-cephem-4-carboxylate (syn isomer, 1.69 g.).

출처 및 근거

ORD 기록
ord-4ffcef068e094370bd3a3af9134d9217
출처 데이터셋
uspto-grants-1984_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04447430

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