Dimethyl Sulfoxide → HCID 89442804, compound
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:14][C@H:15]1[C@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@@H:19]([O:25][C:26](=[O:28])[CH3:27])[C@H:18]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([CH2:36][C:37]3[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][OH:45])=[CH:39][CH:38]=3)[CH:30]=2)[O:17][C@@H:16]1[CH2:46][O:47][C:48](=[O:50])[CH3:49])(=[O:13])[CH3:12].CCN(CC)CC>C(Cl)Cl.CCOCC>[C:11]([O:14][C@H:15]1[C@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@@H:19]([O:25][C:26](=[O:28])[CH3:27])[C@H:18]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([CH2:36][C:37]3[CH:38]=[CH:39][C:40]([CH2:43][CH:44]=[O:45])=[CH:41][CH:42]=3)[CH:30]=2)[O:17][C@@H:16]1[CH2:46][O:47][C:48](=[O:50])[CH3:49])(=[O:13])[CH3:12]Participants
Procedure
Oxalyl chloride (0.086 mL, 1.01 mmol) was added to a solution of DMSO (0.14 mL, 2.0 mmol) in dry DCM (1 mL) at −78° C. under nitrogen atmosphere. The reaction mixture was stirred for 5 min. at the same temperature and then a solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(2-hydroxyethyl)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (0.35 g, 0.6 mmol, prepared by following the procedure as described in WO2011070592), in dry DCM (3 mL) was added. The reaction mixture was stirred at the same temperature for 20 min. NEt3 (0.41 mL, 3.0 mmol) was added and the reaction mixture was allowed to come to r.t. Pet.ether (3 mL) was added to the reaction mixture and the solid was filtered. The filterate was concentrated in vacuo to afford the title compound, which was used as such in next step.
Workup
- additionwas added
- stirringThe reaction mixture was stirred at the same temperature for 20 min
- customto come to r.t
- filtrationthe solid was filtered
- concentrationThe filterate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-64556c8f639146eda4cfd8ed3f13633b
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018249B2
Reaction notes
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