Phosphorus oxychloride → 7-(2-Methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid

HRID 1154831노트

반응식

HRID 1154831 반응식
[NH2:1][CH:2]1[C:13](=[O:14])[N:4]2[CH:5]([C:10]([OH:12])=[O:11])[CH:6]([OH:9])[CH2:7][S:8][C@H:3]12.C[Si](CC(N)=O)(C)C.[CH3:23][O:24][N:25]=[C:26]([C:30]([O:36][CH2:37][CH3:38])([O:33][CH2:34][CH3:35])[CH2:31][Br:32])[C:27](O)=[O:28].P(Cl)(Cl)(Cl)=O>C(Cl)Cl.CN(C)C=O>[CH3:23][O:24][N:25]=[C:26]([C:30]([O:36][CH2:37][CH3:38])([O:33][CH2:34][CH3:35])[CH2:31][Br:32])[C:27]([NH:1][CH:2]1[C:13](=[O:14])[N:4]2[CH:5]([C:10]([OH:12])=[O:11])[CH:6]([OH:9])[CH2:7][S:8][C@H:3]12)=[O:28]

참가 물질

7

반응물 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 13072520(6R)-7-amino-3-hydroxy-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylic acidHCID 543237322-Methoxyimino-3,3-diethoxy-4-bromobutyric acid

생성물 1

HCID 867380937-(2-Methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid수율 44.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

7-Amino-3-hydroxycepham-4-carboxylic acid (1.09 g., purity 84.8%), trimethylsilylacetamide (5.3 g.), 2-methoxyimino-3,3-diethoxy-4-bromobutyric acid (syn isomer, 1.8 g.), phosphorus oxychloride (0.68 ml.), N,N-dimethylformamide (0.55 ml.) and methylene chloride (25 ml.) were treated in a similar manner to that of Example 25 (1) to give 7-(2-methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 1.1 g.).

출처 및 근거

ORD 기록
ord-becc8a413a7748a8a2b16b6e5c2e56c0
출처 데이터셋
uspto-grants-1981_11
특허 번호
US04298529

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