Potassium Carbonate → Tert-butyl 4-((2,2-diethoxyethylamino)methyl)benzo[d]thiazol-2-ylcarbamate
Reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][NH2:6])[CH3:2].Br[CH2:11][C:12]1[C:17]2[N:18]=[C:19]([N:21](C(OC(C)(C)C)=O)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[S:20][C:16]=2[CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][NH:6][CH2:11][C:12]1[C:17]2[N:18]=[C:19]([NH:21][C:22](=[O:23])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[S:20][C:16]=2[CH:15]=[CH:14][CH:13]=1)[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2,2-diethoxyethanamine (8.72 ml, 60.0 mmol) in acetonitrile (300 ml) were added 4-bromomethyl-2-bis(tert-butoxycarbonyl)aminobenzothiazole (Compound XIX-1) (1.33 g, 3.00 mmol) and potassium carbonate (3.14 g, 18.0 mmol) and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue was diluted with ethyl acetate (300 ml) and the mixture was washed with water (300 ml) and brine (200 ml). The organic layer was dried over magnesium sulfate (5 g) and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (eluent: chloroform:methanol=100:0 to 80:20) to obtain the title compound (1.01 g, yield: 85%).
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- additionthe residue was diluted with ethyl acetate (300 ml)
- washthe mixture was washed with water (300 ml) and brine (200 ml)
- dry with materialThe organic layer was dried over magnesium sulfate (5 g)
- filtrationfiltered
- concentrationThe filtrate was concentrated in vacuo
- customthe residue was purified by silica gel column chromatography (eluent: chloroform:methanol=100:0 to 80:20)
Sources & evidence
- ORD record
- ord-32e9348fe64b4f57b255c7f5c05b65dd
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691819B2
Reaction notes
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