Sodium Hydroxide → Ertapenem Sodium

Reaction equation

C1N(CCCS(O)(=O)=O)CCOC1.[CH3:14][C@H:15]1[C:22]([S:23][C@@H:24]2[CH2:28][NH:27][C@H:26]([C:29]([NH:31][C:32]3[CH:33]=[CH:34][CH:35]=[C:36]([C:38]([OH:40])=[O:39])[CH:37]=3)=[O:30])[CH2:25]2)=[C:21]([C:41]([OH:43])=[O:42])[N:20]2[C@H:16]1[C@@H:17]([C@H:44]([OH:46])[CH3:45])[C:18]2=[O:19].[OH-].[Na+:48]>C(OCC)(=O)C>[CH3:14][C@H:15]1[C:22]([S:23][C@@H:24]2[CH2:28][NH:27][C@H:26]([C:29]([NH:31][C:32]3[CH:33]=[CH:34][CH:35]=[C:36]([C:38]([O-:40])=[O:39])[CH:37]=3)=[O:30])[CH2:25]2)=[C:21]([C:41]([OH:43])=[O:42])[N:20]2[C@H:16]1[C@@H:17]([C@H:44]([OH:46])[CH3:45])[C:18]2=[O:19].[Na+:48]

Participants

Procedure

To MOPS buffer solution (prepared from 5.5 g MOPS in 100 mL water and pH adjusted to 6-8.5 with sodium hydroxide), diprotected Ertapenem of formula (IV) (10 g) was added and pH adjusted to 7.5 using aqueous sodium hydroxide solution. To this, ethyl acetate (100 mL) was added and stirred to get clear solution at 10-15° C. CO2 gas was purged for 20 mts. To this Pd/C (20 g, 10%) was added and subjected to hydrogenation with 4.5-5.0 Kg pressure at 5-10° C. After completion of reaction, the reaction mass was filtered and the layers separated. The aqueous layer was subjected to carbon treatment and the pH of the filtrate adjusted to 5.5-6.0 followed by stirring with THF (400 mL) for 10 h. The separated oily layer was slowly added into absolute ethanol (100 mL) under stirring at 5° C. The precipitated solid of ertapenem sodium was filtered, washed with ethanol and dried to yield amorphous form of ertapenem sodium. Dry weight: 4.0 g.