Diisopropylethylamine → HCID 90016372, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:30])=[C:6]([C@:8]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[O:28][CH3:29])([CH3:17])[CH2:9][S:10][C:11]([CH3:16])([CH3:15])[C:12](O)=[O:13])[CH:7]=1.C(N(C(C)C)CC)(C)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:30])=[C:6]([C@@:8]2([CH3:17])[N:18]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=3[O:28][CH3:29])[C:12](=[O:13])[C:11]([CH3:16])([CH3:15])[S:10][CH2:9]2)[CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
To a solution of (R)-2-(2-(5-bromo-2-fluorophenyl)-2-(2,4-dimethoxybenzylamino) propylthio)-2-methylpropanoic acid (2.6 g, 5.2 mmol, Eq: 1.00) and diisopropylethylamine (2.01 g, 2.72 ml, 15.6 mmol, Eq: 3.0) in ethyl acetate (104 ml) was added at 23° C. 1-propanephosphonic acid cyclic anhydride (50% solution in ethyl acetate) (4.96 g, 4.63 ml, 7.79 mmol, Eq: 1.5). The colourless reaction solution was stirred at 23° C. for 2 hours. The reaction mixture was washed with sat NaHCO3-sol., water and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give the crude and nearly pure (R)-5-(5-bromo-2-fluorophenyl)-4-(2,4-dimethoxybenzyl)-2,2,5-trimethylthiomorpholin-3-one (2.45 g, 5.08 mmol, 97.7% yield) as a colourless oil which crystallized in the fridge. MS (ISP): m/z=482.0 [M+H]+ and 484.3 [M+2+H]+.
Workup
- washThe reaction mixture was washed with sat NaHCO3-sol
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-72298cdd8b9648228321b9ded1229826
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273042B2
Reaction notes
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