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

HRID 848374
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HRID 848374 반응식
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:10]([OH:12])=O)[N:8]=1)=[O:2].CN(C)C=O.P(Cl)(Cl)(Cl)=O.Cl.[NH2:32][CH:33]1[C:54](=[O:55])[N:35]2[C:36]([C:41]([O:43][CH2:44][C:45]3[CH:50]=[CH:49][C:48]([N+:51]([O-:53])=[O:52])=[CH:47][CH:46]=3)=[O:42])=[C:37]([Cl:40])[CH2:38][S:39][C@H:34]12>C(OCC)(=O)C.CC(C)=O.O1CCCC1.O>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:10]([NH:32][CH:33]2[C:54](=[O:55])[N:35]3[C:36]([C:41]([O:43][CH2:44][C:45]4[CH:46]=[CH:47][C:48]([N+:51]([O-:53])=[O:52])=[CH:49][CH:50]=4)=[O:42])=[C:37]([Cl:40])[CH2:38][S:39][C@H:34]23)=[O:12])[N:8]=1)=[O:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 545208242-Hexyloxyimino-2-(2-formylaminothiazol-4-yl)acetic acidHCID 703621504-Nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride

생성물 1

HCID 1317124984-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-n-hexyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate수율 90.2%

시약·촉매·용매 4

HCID 180Acetone용매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 2-(2-formamidothiazol-4-yl)-2-n-hexyloxyiminoacetic acid (syn isomer, 3.24 g.), N,N-dimethylformamide (0.951 g.), and phosphoryl chloride (2.00 g.) in ethyl acetate (20 ml.), and a solution of 4-nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride (4 g.) in a mixture of acetone (20 ml.), water (20 ml.) and tetrahydrofuran (400 ml.) were treated in a similar manner to that of Example 21-(1) to give 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-n-hexyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 5.78 g.).

후처리

  1. additionwere treated in a similar manner to that of Example 21-(1)

출처 및 근거

ORD 기록
ord-8236e5a2fd6c42ff94a230ffd83b4c37
출처 데이터셋
uspto-grants-1981_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04294960

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