(Diethylamino)sulfur trifluoride → HCID 117966723, compound
Reaction equation
O[CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@@H:4]([C:15](=[O:29])[NH:16][C@H:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=2)[CH3:18])[CH2:3]1.CCN(S(F)(F)[F:36])CC>C(Cl)Cl>[F:36][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@@H:4]([C:15](=[O:29])[NH:16][C@H:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=2)[CH3:18])[CH2:3]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
A solution of (2R)-tert-butyl 4-hydroxy-2-(((S)-1-(4-(methoxycarbonyl)phenyl)ethyl)carbamoyl)piperidine-1-carboxylate (D61) (261 mg, 0.64 mmol) in DCM (10 ml) cooled at −20° C. was treated with DAST (0.17 ml, 1.28 mmol) and the reaction mixture stirred 1 h at −20° C. then at RT for 18 hrs. DAST (0.17 ml, 1.28 mmol) was added and the mixture further stirred 24 hrs. The reaction was quenched with NaHCO3 sat. sol. and extracted with DCM (3×10 ml), dried over MgSO4 and evaporated in vacuo. The residue was loaded onto a SPE-Si cartridge (20 g) eluting with a mixture DCM/EtOAc 90/10. Collected fractions after solvent evaporation afforded the title compound (D62) (89 mg)
Workup
- waitat RT for 18 hrs
- customthe mixture further stirred 24 hrs
- customThe reaction was quenched with NaHCO3 sat. sol.
- extractionextracted with DCM (3×10 ml)
- dry with materialdried over MgSO4
- customevaporated in vacuo
- washeluting with a mixture DCM/EtOAc 90/10
- customCollected fractions after solvent evaporation
Sources & evidence
- ORD record
- ord-83ddfb4ecf4446bb8617fd9e68f1bc8c
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181279B2
Reaction notes
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