Dimethyl Sulfoxide → HCID 86701123, compound
Reaction equation
CS(C)=O.C(Cl)(C(Cl)=O)=O.[CH2:11]([O:18][C@@H:19]1[C@@H:27]([CH2:28][OH:29])[O:26][C@H:25]2[C@H:21]([N:22]=[C:23]([N:30]([CH2:38][CH:39]=[CH2:40])[C:31](=O)OC(C)(C)C)[S:24]2)[C@H:20]1[O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[CH2:11]([O:18][C@@H:19]1[C@@H:27]([CH:28]=[O:29])[O:26][C@H:25]2[C@H:21]([N:22]=[C:23]([N:30]([CH3:31])[CH2:38][CH:39]=[CH2:40])[S:24]2)[C@H:20]1[O:41][CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
A solution of DMSO (4.1 g, 52 mmol) in dry dichloromethane (70 mL) was treated with (COCl)2 (4.9 g, 40 mmol) at −78° C. for 30 minutes, followed by addition of 139 (3 g, 6.6 mmol) in dichloromethane (10 mL) slowly. The resulting solution was stirred for 3 hours at −30° C., then cooled down to −78° C. again and triethylamine (10 g, 90 mmol) was added. After additional 30 minutes at −50° C., the resulting mixture was quenched by water (50 mL), and the aqueous layer was extracted with dichloromethane (3×30 mL). The combined organic layer was dried over sodium sulfate, and concentrated to afford crude the title compound as light yellow syrup, which was used in the next step without further purification.
Workup
- temperaturecooled down to −78° C. again
- waitAfter additional 30 minutes at −50° C.
- customthe resulting mixture was quenched by water (50 mL)
- extractionthe aqueous layer was extracted with dichloromethane (3×30 mL)
- dry with materialThe combined organic layer was dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-01ab46a60af7435a9796ddf14b2df6db
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901087B2
Reaction notes
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