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Phosphorus oxychloride → 7-[2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-2-methyl-3-cephem-4-carboxylic acid

HRID 256449
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HRID 256449 반응식
[NH2:1][CH:2]1[C:13](=[O:14])[N:4]2[C:5]([C:10]([OH:12])=[O:11])=[CH:6][CH:7]([CH3:9])[S:8][C@H:3]12.C[Si](CC(N)=O)(C)C.P(Cl)(Cl)(Cl)=O.[CH:28]([NH:30][C:31]1[S:32][C:33]([Br:43])=[C:34]([C:36](=[N:40][O:41][CH3:42])[C:37](O)=[O:38])[N:35]=1)=[O:29]>C(OCC)(=O)C.CN(C)C=O>[CH:28]([NH:30][C:31]1[S:32][C:33]([Br:43])=[C:34]([C:36](=[N:40][O:41][CH3:42])[C:37]([NH:1][CH:2]2[C:13](=[O:14])[N:4]3[C:5]([C:10]([OH:12])=[O:11])=[CH:6][CH:7]([CH3:9])[S:8][C@H:3]23)=[O:38])[N:35]=1)=[O:29]
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참가 물질

7

반응물 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 128022512-Methyl-7-amino-3-cephem-4-carboxylic acidHCID 538011022-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetic acid

생성물 1

HCID 1317153637-[2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-2-methyl-3-cephem-4-carboxylic acid수율 78.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매2회

실험 절차

A solution of 7-amino-2-methyl-3-cephem-4-carboxylic acid (1.0 g.) and trimethylsilylacetamide (3.7 g.) in dry ethyl acetate (30 ml.) and a solution of dimethylformamide (0.47 ml.), phosphoryl chloride (0.56 ml.) and 2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 1.6 g.) in dry ethyl acetate (11.6 ml.) were treated in a similar manner to that of Example 1-(1) to give 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-2-methyl-3-cephem-4-carboxylic acid (syn isomer, 1.85 g.).

출처 및 근거

ORD 기록
ord-56d58639de7547378db8a1ca70e36e4d
출처 데이터셋
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04703046

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