Pyridine → Tert-butyl 4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2-oxide
Reaction equation
[S:1](Cl)(Cl)=[O:2].[OH:5][CH:6]([CH3:17])[CH:7]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:8].N1C=CC=CC=1.C(OCC)(=O)C>C(#N)C.CN(C)C1C=CN=CC=1>[CH3:8][CH:7]1[CH:6]([CH3:17])[O:5][S:1](=[O:2])[N:9]1[C:10]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:16]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -40 °C
Procedure
A stirred solution of thionyl chloride (4.1 mL, 56.8 mmol) in acetonitrile (30 mL) is cooled to −45° C. A solution of tert-butyl (3-hydroxybutan-2-yl)carbamate (4.3 g, 22.7 mmol) in acetonitrile (40 mL) is added by syringe over about 10 min, keeping the internal temperature below −40° C. When the addition is completed, 4-dimethylamino pyridine (278 mg, 2.3 mmol) is added. Then pyridine (9.2 mL, 114 mmol) is added dropwise by syringe, keeping the temperature below −40° C. The reaction mixture is stirred at −40° C. for 1 hr. Ethyl acetate (70 mL) is added to the suspension and the mixture is filtered at −35° C. The solid is washed with EtOAc and the filtrates are combined. Saturated Na2HPO4 solution (40 mL) is added and the mixture is stirred vigorously for 30 min. The organic layer is separated, washed with 1M NaHSO4, dried (MgSO4) and concentrated to afford the title compound (4.8 g, 90%) as an oil.
Workup
- customthe internal temperature below −40° C
- additionWhen the addition
- customthe temperature below −40° C
- filtrationthe mixture is filtered at −35° C
- washThe solid is washed with EtOAc
- additionSaturated Na2HPO4 solution (40 mL) is added
- stirringthe mixture is stirred vigorously for 30 min
- customThe organic layer is separated
- washwashed with 1M NaHSO4
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-91be77cdd80640c08b99a739bc5a4dfa
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073926B2
Reaction notes
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