HCID 131721049, compound → HCID 131721048, compound

HRID 1459606Notes

Reaction equation

HRID 1459606 reaction equation
[N:1]([C:4]1([C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:45])([P:37]([O:42][O:43][CH3:44])([O:39][O:40][CH3:41])=[O:38])[P:29]([O:34][O:35][CH3:36])([O:31][O:32][CH3:33])=[O:30])=[O:22])[C:19](=[O:20])[N:6]2[C:7]([C:16]([OH:18])=[O:17])=[C:8]([CH2:11][O:12][C:13](=[O:15])[NH2:14])[CH2:9][S:10][C@H:5]12)=[N+]=[N-].[H][H]>[Pt]=O>[NH2:1][C:4]1([C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:45])([P:37]([O:42][O:43][CH3:44])([O:39][O:40][CH3:41])=[O:38])[P:29]([O:34][O:35][CH3:36])([O:31][O:32][CH3:33])=[O:30])=[O:22])[C:19](=[O:20])[N:6]2[C:7]([C:16]([OH:18])=[O:17])=[C:8]([CH2:11][O:12][C:13](=[O:15])[NH2:14])[CH2:9][S:10][C@H:5]12

Participants

4

Reactant 2

HCID 131721049HCID 131721049, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131721048HCID 131721048, compound

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

The 7-azido-7-{[5-hydroxy-5,5-bis(dimethoxyphosphono)-1-pentylamino]-carbonyl}-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid, obtained as described in Example 30, is hydrogenated at atmospheric pressure with hydrogen in the presence of platinum oxide as catalyst and gives 7-amino-7-{[5-hydroxy-5,5-bis(dimethoxyphosphono)-1-pentylamino]-carbonyl}-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid. Reaction of the latter with 2-thienylacetyl chloride and pyridine yields 7-(2-thienyl-acetamido)-7-{[5-hydroxy-5,5-bis(dimethoxyphosphono)-1-pentylamino]-carbonyl}-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid.

Sources & evidence

ORD record
ord-65980e2d23d748aca54290c8b7d0d9d3
Source dataset
uspto-grants-1998_12
Patent number
US05854227

Reaction notes

Loading…