Dimethyl Sulfoxide → HCID 15523989, compound
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([S:14][CH2:15][CH2:16][C@@H:17]([C:29]([NH:31][C@H:32]([C:42]([O:44][CH3:45])=[O:43])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH2:40][OH:41])=[O:30])[NH:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])(=[O:13])[CH3:12].CCN(CC)CC>C(Cl)Cl.CCOC(C)=O>[C:11]([S:14][CH2:15][CH2:16][C@@H:17]([C:29]([NH:31][C@H:32]([C:42]([O:44][CH3:45])=[O:43])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH:40]=[O:41])=[O:30])[NH:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])(=[O:13])[CH3:12]Participants
7
Conditions
- Temperature
- -78 °C
Procedure
To a solution of oxalyl chloride (192 μL, 2.2 mmol) in CH2Cl2 (3 mL) cooled at −78° C. was added DMSO (312 μL, 4.4 mmol). After stirring at −78° C. for 5 minutes, a solution of the title compound of step (I) (790 mg, 1.572 mmol) in CH2Cl2 (9 mL) was added dropwise. The resultant white suspension was stirred at −78° C. for 30 minutes, before Et3N (0.964 mL, 6.916 mmol) was added. The reaction mixture was warmed up at −30° C. and stirred for 1 hour. The mixture was diluted with EtOAc (100 mL), washed with 5% KHSO4 (2×), sat. NaHCO3 (1×), H2O (2×), brine, dried (MgSO4), filtered and concentrated in vacuo to give 0.77 g (98%) of the title compound of this step as a white foam.
Workup
- additionwas added
- temperatureThe reaction mixture was warmed up at −30° C.
- stirringstirred for 1 hour
- washwashed with 5% KHSO4 (2×), sat. NaHCO3 (1×), H2O (2×), brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-d663cb63f5554aa99d547c6c518031b8
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06235922B1
Reaction notes
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