Ammonium trifluoroacetate → HCID 178489843, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=O)[CH2:10][NH:11][C:12]([CH:14]2[O:19][CH2:18][CH2:17][N:16]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:15]2)=O)[CH:6]=[CH:7][CH:8]=1.FC(F)(F)C([O-])=O.[NH4+:35]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:35]=[C:12]([CH:14]3[O:19][CH2:18][CH2:17][N:16]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:15]3)[NH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1Participants
3
Conditions
- Temperature
- 150 °C
Procedure
A mixture of N-{2-[3-(methyloxy)phenyl]-2-oxoethyl}-4-(phenylmethyl)-2-morpholinecarboxamide (1.6 g, 4.34 mmol) and ammonium trifluoroacetate (2.85 g, 21.71 mmol) was stirred for 0.75 hours at 150° C. The LCMS indicated that the starting material was consumed. The desired product was contained in the residue. Water (50 mL) was added to the residue, and the resulting mixture was extracted with EtOAc (3×50 mL). The organics were dried (Na2SO4), filtered, and concentrated to afford the title compound (1.56 g) as a brown oil. LC-MS (ES) m/z=350 [M+H]+.
Workup
- customwas consumed
- additionWater (50 mL) was added to the residue
- extractionthe resulting mixture was extracted with EtOAc (3×50 mL)
- dry with materialThe organics were dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-672ef83b32d3428b80d005d8c3c697ec
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697685B2
Reaction notes
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