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

HRID 1702076Notes

Reaction equation

HRID 1702076 reaction equation
[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].P(Cl)(Cl)(Cl)=O.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]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 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

Product 1

HCID 867380937-(2-Methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acidYield 68.7%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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), phosphorus 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.

Sources & evidence

ORD record
ord-007ab9e685d34d3e867e436fa69d4771
Source dataset
uspto-grants-1983_04
Patent number
US04379922

Reaction notes

Loading…