Dimethyl Sulfoxide → Ethyl 2-(4-(tert-butoxycarbonyl)piperazin-1-YL)thiazole-4-carboxylate
Reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.ClC1S[C:17]([C:20](OC)=[O:21])=CN=1.[C:24]1([C:35]2CCCCCCCCCC=2)[CH2:34]CCCCCCCN[N:25]=1.[OH2:46].[CH3:47][S:48](C)=O>[I-].[K+]>[CH2:20]([O:21][C:35]([C:24]1[N:25]=[C:47]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)[S:48][CH:34]=1)=[O:46])[CH3:17]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
1,1-Dimethylethyl 1-piperazinecarboxylate (1.86 g, 10 mmol), methyl 2-chloro-5-thiazolecarboxylate (1.92 g, 10.0 mmol), diazabicycloundecene (1.5 mL, 10 mmol) and a catalytic amount of potassium iodide (2 mg) were dissolved in 10 mL of dry dimethylsulfoxide and warmed to 80° C. for 16 h. The warm solution was added dropwise with stirring to 200 mL of cold water. The reaction mixture was extracted with diethyl ether. The resulting extract was washed with water and brine, dried over magnesium sulfate and concentrated under reduced pressure to give 3.23 g of a yellow oil which solidified on standing. The solid was recrystallized from diethyl ether/hexanes to give 1.0 g of the title compound as light yellow crystals. This compound was of sufficient purity to use in subsequent reactions.
Workup
- additionThe warm solution was added dropwise
- extractionThe reaction mixture was extracted with diethyl ether
- extractionThe resulting extract
- washwas washed with water and brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-535b69e7c81f40d2ba571632275fb6b9
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08586611B2
Reaction notes
Loading…