Trifluoroacetic acid → (2R)-2-amino-N-{2-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-5-pyrimidinyl}butanamide
Reaction equation
[CH3:1][C:2]1([CH3:32])[C:6]2[C:7]([O:11][C:12]3[N:17]=[CH:16][C:15]([NH:18][C:19]([C@H:21]([NH:24]C(=O)OC(C)(C)C)[CH2:22][CH3:23])=[O:20])=[CH:14][N:13]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1.C(O)(C(F)(F)F)=O>ClCCl>[NH2:24][C@H:21]([CH2:22][CH3:23])[C:19]([NH:18][C:15]1[CH:14]=[N:13][C:12]([O:11][C:7]2[C:6]3[C:2]([CH3:1])([CH3:32])[CH2:3][O:4][C:5]=3[CH:10]=[CH:9][CH:8]=2)=[N:17][CH:16]=1)=[O:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1,1-dimethylethyl {(1R)-1-[({2-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-5-pyrimidinyl}amino)carbonyl]propyl}carbamate (Intermediate 66, 4.4 mg) in dichloromethane (1 ml) cooled to 0° C. TFA (0.019 ml, 0.249 mmol) was added dropwise. The mixture reaction was stirred at 0° C. for 1.5 hours. The solvent and the TFA were evaporated. The mixture was diluted with dichloromethane (5 ml) and neutralized with an aqueous saturated solution of NaHCO3 (5 ml). The organic layer was separated, dried over sodium sulphate, filtered end evaporated to afford the title compound (3 mg) which was directly used in the next step
Workup
- customThe mixture reaction
- customThe solvent and the TFA were evaporated
- additionThe mixture was diluted with dichloromethane (5 ml)
- customThe organic layer was separated
- dry with materialdried over sodium sulphate
- filtrationfiltered end
- customevaporated
Sources & evidence
- ORD record
- ord-a9ed9f904f894cb7a1d09dd310a0122d
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346790B2
Reaction notes
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