Dichloromethane → Tert-butyl 2-(4-((2,2-difluorobenzo[d][1,3]dioxole-5-carboxamido)methyl)piperidin-1-yl)ethylcarbamate
Reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:5][CH2:4]1.C(Cl)Cl.[F:22][C:23]1([F:35])[O:27][C:26]2[CH:28]=[CH:29][C:30]([C:32](Cl)=[O:33])=[CH:31][C:25]=2[O:24]1.C([O-])(O)=O.[Na+]>CCOC(C)=O.C1COCC1>[F:35][C:23]1([F:22])[O:27][C:26]2[CH:28]=[CH:29][C:30]([C:32]([NH:1][CH2:2][CH:3]3[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[CH2:5][CH2:4]3)=[O:33])=[CH:31][C:25]=2[O:24]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -20 °C
Procedure
A solution of tert-butyl 2-(4-(aminomethyl)piperidin-1-yl)ethylcarbamate (50 mg, 0.19 mmol) and TEA (135 μL, 0.972 mmol) in a mixture of 1:1 CH2Cl2:THF (2.5 mL) was treated with 2,2-difluorobenzo[d][1,3]dioxole-5-carbonyl chloride (51 mg, 0.23 mmol). The resulting solution was stirred overnight, then transferred to a test tube containing saturated aqueous NaHCO3 (4 mL) and EtOAc (4 mL). The biphasic mixture was mixed vigorously and allowed to separate for 15 minutes. After separation, the mixture was cooled to −20° C. until the aqueous layer was frozen. The organic layer was then poured off and the solvent was removed under reduced pressure at 50° C. The resulting residue was purified by HiTOPs.
Workup
- customtransferred to a test tube
- additionThe biphasic mixture was mixed vigorously
- customto separate for 15 minutes
- customAfter separation
- temperaturewas frozen
- additionThe organic layer was then poured off
- customthe solvent was removed under reduced pressure at 50° C
- customThe resulting residue was purified by HiTOPs
Sources & evidence
- ORD record
- ord-8939946db5b144559c8d3974fb28389b
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08377968B2
Reaction notes
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