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Phosphorus oxychloride → 4-Nitrobenzyl 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

HRID 256446
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HRID 256446 반응식
[NH2:1][CH:2]1[C:22](=[O:23])[N:4]2[C:5]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)=[O:10])=[CH:6][CH2:7][S:8][C@H:3]12.C[Si](CC(N)=O)(C)C.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.P(Cl)(Cl)(Cl)=O.[CH:49]([NH:51][C:52]1[S:53][C:54]([Br:64])=[C:55]([C:57](=[N:61][O:62][CH3:63])[C:58](O)=[O:59])[N:56]=1)=[O:50]>C(OCC)(=O)C.C(OCC)C.C(O)(C)C.CN(C)C=O>[CH:49]([NH:51][C:52]1[S:53][C:54]([Br:64])=[C:55]([C:57](=[N:61][O:62][CH3:63])[C:58]([NH:1][CH:2]2[C:22](=[O:23])[N:4]3[C:5]([C:9]([O:11][CH2:12][C:13]4[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=4)=[O:10])=[CH:6][CH2:7][S:8][C@H:3]23)=[O:59])[N:56]=1)=[O:50]
참가 물질실험 절차출처 및 근거반응 노트

참가 물질

10

반응물 5

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 11708267BistrimethylsilylacetamidHCID 12775080p-Nitrobenzyl 7-amino-3-cephem-4-carboxylateHCID 538011022-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetic acid

생성물 1

HCID 131715359
4-Nitrobenzyl 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate
수율 43.1%

시약·촉매·용매 4

HCID 3283Diethyl Ether용매HCID 3776Isopropanol용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매2회

실험 절차

A solution of 4-nitrobenzyl 7-amino-3-cephem-4-carboxylate (3.3 g.), trimethylsilylacetamide (6.4 g.) and bis(trimethylsilyl)acetamide (6.0 g.) in dry ethyl acetate (100 ml.) and a solution of dimethylformamide (0.9 ml.), phosphoryl chloride (1.1 ml.) and 2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 5.1 g.) in dry ethyl acetate (5 ml.) were treated in a similar manner to that of Example 1-(1) (isopropyl alcohol was used for pulverization instead of diethyl ether) to give 4-nitrobenzyl 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 2.65 g.).

출처 및 근거

ORD 기록
ord-6497734417d3470aae8799026e4ae1aa
출처 데이터셋
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04703046

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