Trifluoroacetic acid → (2R)-2-amino-2-methyl-N-[6-(3-methylchroman-5-yl)oxy-3-pyridyl]butanamide
Reaction equation
[CH3:1][C@:2]([NH:26]C(=O)OC(C)(C)C)([C:5](=[O:25])[NH:6][C:7]1[CH:8]=[N:9][C:10]([O:13][C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH2:16][CH:17]([CH3:24])[CH2:18][O:19]3)=[CH:11][CH:12]=1)[CH2:3][CH3:4].C(O)(C(F)(F)F)=O>ClCCl>[NH2:26][C@:2]([CH3:1])([CH2:3][CH3:4])[C:5]([NH:6][C:7]1[CH:8]=[N:9][C:10]([O:13][C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH2:16][CH:17]([CH3:24])[CH2:18][O:19]3)=[CH:11][CH:12]=1)=[O:25]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In a 50 mL round-bottomed flask tert-butyl N-[(1R)-1-methyl-1-[[6-(3-methylchroman-5-yl)oxy-3-pyridyl]carbamoyl]propyl]carbamate (Intermediate 146, 55.8 mg, 0.104 mmol) was dissolved in Dichloromethane (3 mL) to give a pale yellow solution. The reaction mixture was cooled at 0° C. and TFA (2 mL, 26.0 mmol) was added. The reaction mixture was stirred at 0° C. for 2 hours. The reaction mixture was evaporated in vacuo to give the crude product as a yellow oil. The sample was charged on a 2 g SCX cartridge. It was then flushed with 36 mL of MeOH followed by 25 mL of 2M solution of ammonia in MeOH. The ammonia eluate was evaporated in vacuo affording the title compound (32.9 mg) as pale yellow oil.
Workup
- customto give a pale yellow solution
- customThe reaction mixture was evaporated in vacuo
- customto give the crude product as a yellow oil
- additionThe sample was charged on a 2 g SCX cartridge
- customIt was then flushed with 36 mL of MeOH
- customThe ammonia eluate was evaporated in vacuo
Sources & evidence
- ORD record
- ord-e086e393c35848d297f62755dec84382
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346790B2
Reaction notes
Loading…