Dichloromethane → HCID 45111074, compound
Reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[N:4]=[C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C@H:15]([CH3:19])[C:16](O)=[O:17])=[CH:11][CH:10]=2)[S:6][CH:7]=1.C(Cl)Cl.[CH3:25][S:26]([NH2:29])(=[O:28])=[O:27]>>[CH3:25][S:26]([NH:29][C:16](=[O:17])[C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:5]2[S:6][CH:7]=[C:3]([C:2]([F:21])([F:20])[F:1])[N:4]=2)=[CH:10][CH:11]=1)[CH3:19])(=[O:28])=[O:27]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (2S)-2-4-{[4-trifluoromethyl)-1,3-thiazol-2yl]amino}phenyl)propanoic acid (3) (0.1 g, 0.32 mmol) in dry CH2Cl2 (2 mL) CDI (0.055 g, 0.34 mmol) was added and the resulting solution was stirred for 1 h at T=0° C. After ice-water bath removal methanesulfonamide (0.032 g, 0.34 mmol) and TEA (40 μl, 0.29 mmol) were added and the resulting mixture was stirred at room temperature for 12 h. At the complete disappearance of the starting material, a buffer H3PO4/H2PO4− solution (pH=2.0, 5 ml) was added and the reaction mixture was trasferred into a reparatory funnel. The two phases were separated and the organic one washed with the same buffer (3×5 mL), dried over Na2SO4 and evaporated under vacuum to give a crude which was purified by flash chromatography. Pure compound 11 (0.089 g, 0.23 mol) was isolated as a yellow oil (71%).
Workup
- additionwere added
- stirringthe resulting mixture was stirred at room temperature for 12 h
- customthe reaction mixture was trasferred into a reparatory funnel
- customThe two phases were separated
- washthe organic one washed with the same buffer (3×5 mL)
- dry with materialdried over Na2SO4
- customevaporated under vacuum
- customto give a crude which
- customwas purified by flash chromatography
Sources & evidence
- ORD record
- ord-b4f8321b20cc4027a02a04d050a1106d
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08624036B2
Reaction notes
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