Dimethyl Sulfoxide → HCID 15667301, compound
Reaction equation
FC(F)(F)C(O[C:6](=[O:11])[C:7](F)(F)F)=O.CS(C)=O.ClCCCS(NCC(C[CH:47]([OH:49])C)CSCCCCCCCCCCCCCCCC)(=O)=O.[Cl:50][CH2:51][CH2:52][CH2:53][S:54]([NH:57][CH2:58][CH:59](CC(=O)C)[CH2:60][O:61][C:62](=[O:82])[NH:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH3:81])(=[O:56])=[O:55].C([N:89](CC)CC)C>ClCCl>[Cl:50][CH2:51][CH2:52][CH2:53][S:54]([NH:57][CH2:58][CH:59]([O:11][C:6]1[CH:7]=[CH:47][O:49][N:89]=1)[CH2:60][O:61][C:62](=[O:82])[NH:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH3:81])(=[O:55])=[O:56]Participants
7
Conditions
- Temperature
- -78 °C
Procedure
To a cooled solution of 0.19 ml (1.33 mM) of trifluoroacetic anhydride in 20 ml of dichloromethane at -78° C. is added 0.19 ml (2.66 mM) of dimethylsulfoxide and the mixture is stirred at -78° C. for 5 minutes. To the reaction mixture is added a solution of 428 mg (0.83 mM) of 1-(3-chloropropylsulfonylamino)-2-(2-hydroxypropan-1-yl)-3-n-hexadecylthiopropane ml5 in 2 ml of dichloromethane with stirring and the mixture is stirred at -70° C. for an additional 15 minutes. 3.50 ml (24.9 mM) of triethylamine is added and the mixture is allowed to react by the same procedure as described in (132) and 213 mg (41.6% yield) of the titled compound III m2 is obtained.
Workup
- stirringwith stirring
- stirringthe mixture is stirred at -70° C. for an additional 15 minutes
- customto react by the same procedure
Sources & evidence
- ORD record
- ord-1aee479c91fc4b77b9dc85e2168c9e5f
- Source dataset
- uspto-grants-1992_08
- Patent number
- US05138067
Reaction notes
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