Sodium Lauryl Sulfate → Tacrolimus
Reaction equation
[CH3:1][C@H:2]1[CH2:33][C:32]([CH3:34])=[CH:31][C@@H:30]([CH2:35][CH:36]=[CH2:37])[C:28](=[O:29])[CH2:27][C@H:26]([OH:38])[C@@H:25]([CH3:39])[C@@H:24](/[C:40](/[CH3:51])=[CH:41]/[C@H:42]2[CH2:47][C@@H:46]([O:48][CH3:49])[C@H:45]([OH:50])[CH2:44][CH2:43]2)[O:23][C:21](=[O:22])[C@H:20]2[N:15]([CH2:16][CH2:17][CH2:18][CH2:19]2)[C:13](=[O:14])[C:11](=[O:12])[C@:9]2([OH:52])[O:10][C@@H:5]([C@@H:6]([O:54][CH3:55])[CH2:7][C@H:8]2[CH3:53])[C@@H:4]([O:56][CH3:57])[CH2:3]1.O.S([O-])(OCCCCCCCCCCCC)(=O)=O.[Na+]>>[CH3:1][C@H:2]1[CH2:33][C:32]([CH3:34])=[CH:31][C@@H:30]([CH2:35][CH:36]=[CH2:37])[C:28](=[O:29])[CH2:27][C@H:26]([OH:38])[C@@H:25]([CH3:39])[C@@H:24](/[C:40](/[CH3:51])=[CH:41]/[C@H:42]2[CH2:47][C@@H:46]([O:48][CH3:49])[C@H:45]([OH:50])[CH2:44][CH2:43]2)[O:23][C:21](=[O:22])[C@H:20]2[N:15]([CH2:16][CH2:17][CH2:18][CH2:19]2)[C:13](=[O:14])[C:11](=[O:12])[C@:9]2([OH:52])[O:10][C@@H:5]([C@@H:6]([O:54][CH3:55])[CH2:7][C@H:8]2[CH3:53])[C@@H:4]([O:56][CH3:57])[CH2:3]1Participants
3
Procedure
Subsequently an analogous procedure was used to prepare the monooxime of tacrolimus. Tacrolimus was provided as a solid mixture in a capsule containing 1.02 mg of tacrolimus monohydrate and approximately a 6-fold excess of sodium dodecyl sulfate (SDS). The solid mixture from 30 capsules was combined and extracted 4 times with 12 ml each time of ethyl acetate. The combined organic extracts were concentrated under a vacuum to give 49 mg of crude tacrolimus which was used directly in the following reaction.
Workup
- extractionextracted 4 times with 12 ml each time of ethyl acetate
- concentrationThe combined organic extracts were concentrated under a vacuum
Sources & evidence
- ORD record
- ord-dba09bd91db0482aa3e759b8721da683
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08030458B2
Reaction notes
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