(6R)-7-amino-3-hydroxy-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylic acid → 7-(2-Methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid

HRID 1154836Notes

Reaction equation

HRID 1154836 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:8]([O:14][CH2:15][CH3:16])([O:11][CH2:12][CH3:13])[CH2:9][Br:10])[C:5](Cl)=[O:6].[NH2:17][CH:18]1[C:29](=[O:30])[N:20]2[CH:21]([C:26]([OH:28])=[O:27])[CH:22]([OH:25])[CH2:23][S:24][C@H:19]12>>[CH3:1][O:2][N:3]=[C:4]([C:8]([O:14][CH2:15][CH3:16])([O:11][CH2:12][CH3:13])[CH2:9][Br:10])[C:5]([NH:17][CH:18]1[C:29](=[O:30])[N:20]2[CH:21]([C:26]([OH:28])=[O:27])[CH:22]([OH:25])[CH2:23][S:24][C@H:19]12)=[O:6]

Participants

3

Reactant 2

HCID 13072520(6R)-7-amino-3-hydroxy-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylic acidHCID 542161602-Methoxyimino-3,3-diethoxy-4-bromobutyryl chloride

Product 1

HCID 867380937-(2-Methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acidYield 118.2%

Procedure

2-Methoxyimino-3,3-diethoxy-4-bromobutyryl chloride (syn isomer, 400.5 g) and 7-amino-3-hydroxycepham-4-carboxylic acid (230 g) were treated in a similar manner to that of Example 41 to give 7-(2-methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 621 g).

Sources & evidence

ORD record
ord-7c44076509d44c508d0d19cbf481f41c
Source dataset
uspto-grants-1981_11
Patent number
US04298529

Reaction notes

Loading…