Lactic Acid → HCID 131723760, compound
Reaction equation
[C:1]([OH:6])(=[O:5])[CH:2]([CH3:4])[OH:3].[CH3:7][NH:8][C@@H:9]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C@H:12]([C:19]2[CH:20]=[CH:21][C:22]([Cl:26])=[C:23]([Cl:25])[CH:24]=2)[CH2:11][CH2:10]1>>[CH3:7][NH:8][C@@H:9]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C@H:12]([C:19]2[CH:20]=[CH:21][C:22]([Cl:26])=[C:23]([Cl:25])[CH:24]=2)[CH2:11][CH2:10]1.[C:1]([O-:6])(=[O:5])[C@H:2]([CH3:4])[OH:3]Participants
Procedure
Sertraline hydrochloride (300 g) was slurried in a 3:1 mixture of water (3 liters) and ethyl acetate (1 liter). The pH of the slurry was adjusted to 8.0 by the addition approximately 1 liter of 1N sodium hydroxide solution. The free base of sertraline partitioned into the ethyl acetate phase. The two phases were allowed to separate completely by allowing the biphasic solution to stand overnight without agitation. The ethyl acetate layer was then separated and washed twice with 3 liters of deionized water to remove chloride ions. The final ethyl acetate layer containing sertraline base was concentrated to 300 mL under vacuum to remove residual water. The ethyl acetate solution containing sertraline base was heated to 40° C. L-lactic acid was dissolved in ethyl acetate to form a 7.5 M solution. The lactic acid solution was added to the sertraline base solution in small portions with constant agitation. The mixture was allowed to stir and granulate overnight (16-20 hours). The crystals were filtered and washed 4 times with an equal volume (200 mL each) of ethyl acetate. The crystals were dried overnight in a vacuum oven at 40° C. The yield was 97%. mp 153° C.
Workup
- custom(16-20 hours)
- filtrationThe crystals were filtered
- washwashed 4 times with an equal volume (200 mL each) of ethyl acetate
- customThe crystals were dried overnight in a vacuum oven at 40° C
Sources & evidence
- ORD record
- ord-6b969fa19f644f6bad469f568b5a3738
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06517866B1
Reaction notes
Loading…