Ammonia → 6-(1-Hydroxyethyl)-4-methyl-7-oxo-3-({5-[(sulfamoylamino)methyl]pyrrolidin-3-yl}sulfanyl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid--water (1/1)
Reaction equation
[CH3:1][C@H:2]1[C:9]([S:10][C@@H:11]2[CH2:15][NH:14][C@H:13]([CH2:16][NH:17][S:18]([NH2:21])(=[O:20])=[O:19])[CH2:12]2)=[C:8]([C:22]([OH:24])=[O:23])[N:7]2[C@H:3]1[C@@H:4]([C@H:25]([OH:27])[CH3:26])[C:5]2=[O:6].N>O>[CH3:1][C@H:2]1[C:9]([S:10][C@@H:11]2[CH2:15][NH:14][C@H:13]([CH2:16][NH:17][S:18]([NH2:21])(=[O:20])=[O:19])[CH2:12]2)=[C:8]([C:22]([OH:24])=[O:23])[N:7]2[C@H:3]1[C@@H:4]([C@H:25]([OH:27])[CH3:26])[C:5]2=[O:6].[OH2:6]Participants
4
Procedure
Doripenem (50 g) was dissolved in water (300 ml) by adding ammonia drop-wise to attain a pH of 8.5 to 9 at 15° to 20° C. The solution was treated with activated carbon (5 g) followed by micron filtration using a membrane (0.25 microns). The pH of the filtrate was adjusted to 5 to 5.5 with aqueous formic acid at 10° to 20° C. The mixture was stirred at 0° to 5° C. for 4 to 5 hours. Isopropyl alcohol (150 ml) was added slowly to the mixture and stirred for about 12 hours at 0° to 5° C. The mixture was filtered and dried at 40° to 50° C. to obtain the title compound.
Workup
- customat 15° to 20° C
- additionThe solution was treated with activated carbon (5 g)
- filtrationfollowed by micron filtration
- customwas adjusted to 5 to 5.5 with aqueous formic acid at 10° to 20° C
- additionIsopropyl alcohol (150 ml) was added slowly to the mixture
- stirringstirred for about 12 hours at 0° to 5° C
- filtrationThe mixture was filtered
- customdried at 40° to 50° C.
Sources & evidence
- ORD record
- ord-d3bdc0038b2b4ffe8cca1bb7b0b6ab5b
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445673B2
Reaction notes
Loading…