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Phosphorus oxychloride → 7-[2-(2-Formamidothiazol-4-yl)-2-(2-chloroethoxyimino)acetamido]-3-cephem-4-carboxylic acid

HRID 621324
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HRID 621324 반응식
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][CH2:16][Cl:17])[C:10]([OH:12])=O)[N:8]=1)=[O:2].P(Cl)(Cl)(Cl)=O.[NH2:23][CH:24]1[C:34](=[O:35])[N:26]2[C:27]([C:31]([OH:33])=[O:32])=[CH:28][CH2:29][S:30][C@H:25]12.C[Si](C([Si](C)(C)C)C(N)=O)(C)C>C(OCC)(=O)C.CN(C)C=O>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][CH2:16][Cl:17])[C:10]([NH:23][CH:24]2[C:34](=[O:35])[N:26]3[C:27]([C:31]([OH:33])=[O:32])=[CH:28][CH2:29][S:30][C@H:25]23)=[O:12])[N:8]=1)=[O:2]
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참가 물질

7

반응물 4

HCID 24813Phosphorus oxychlorideHCID 11708267BistrimethylsilylacetamidHCID 12941984(6R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 539721442-(2-Formamidothiazol-4-yl)-2-(2-chloroethoxyimino)acetic acid

생성물 1

HCID 1317124827-[2-(2-Formamidothiazol-4-yl)-2-(2-chloroethoxyimino)acetamido]-3-cephem-4-carboxylic acid수율 32.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매2회

실험 절차

A solution of 2-(2-formamidothiazol-4-yl)-2-(2-chloroethoxyimino)acetic acid (syn isomer, 3.47 g.), N,N-dimethylformamide (1.1 g.) and phosphoryl chloride (2.3 g.) in ethyl acetate (35 ml.), and a solution of 7-amino-3-cephem-4-carboxylic acid (2.5 g.) and bis(trimethylsilyl)acetamide (12.7 g.) in ethyl acetate (25 ml.) were treated in a similar manner to that of Example 15-(1) to give 7-[2-(2-formamidothiazol-4-yl)-2-(2-chloroethoxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.85 g.).

출처 및 근거

ORD 기록
ord-58a8833370e84b60944c803b1aa6db49
출처 데이터셋
uspto-grants-1989_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04822888

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