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

HRID 1154832노트

반응식

HRID 1154832 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.[CH3:15][O:16][N:17]=[C:18]([C:22]([O:28][CH2:29][CH3:30])([O:25][CH2:26][CH3:27])[CH2:23][Br:24])[C:19](O)=[O:20].O(Cl)Cl.CN(C)C=O>O1CCCC1.CC(C)=O.O>[CH3:15][O:16][N:17]=[C:18]([C:22]([O:28][CH2:29][CH3:30])([O:25][CH2:26][CH3:27])[CH2:23][Br:24])[C:19]([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:20]

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 24646Chlorine monoxideHCID 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 68.7%

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

7-Amino-3-hydroxycepham-4-carboxylic acid (10.9 g, purity 84.8%), 2-methoxyimino-3,3,diethoxy-4-bromobutyric acid (syn isomer, 17.9 g), phosporus oxychloride (6.8 ml), N,N-dimethylformamide (5.5 ml), water (100 ml), acetone (50 ml.) and tetrahydrofuran (44 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, 17.1 g.). The I.R. spectrum and N.M.R. spectrum of the compound were the same as those of Example 28.

출처 및 근거

ORD 기록
ord-2419f0599a8348b38f71d32e9488145b
출처 데이터셋
uspto-grants-1981_11
특허 번호
US04298529

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