Aniline → (R)-methyl 2-phenyl-2-(phenylamino)acetate
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(O[C@@H:13]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:14]([O:16][CH3:17])=[O:15])(=O)=O>CC#N>[C:18]1([C@@H:13]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:14]([O:16][CH3:17])=[O:15])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
Aniline (16.8 mL, 184 mmol) is added to a solution of (S)-methyl 2-(methylsulfonyloxy)-2-phenylacetate (I5) (22.4 g, 92.0 mmol) in CH3CN (50 mL). The mixture is heated under MW irradiation at 120° C. for 5 minutes (UPLC-MS monitoring: complete conversion). The resulting crude is partitioned between EtOAc (200 mL) and 1N HCl (200 mL) and the aqueous phase is extracted with EtOAc (3×200 mL). The combined organic layers are dried over Na2SO4, filtered and evaporated under vacuum to obtain 20.3 g of a pale yellow solid (92% yield), which is used in the next step without any additional purification.
Workup
- customThe resulting crude is partitioned between EtOAc (200 mL) and 1N HCl (200 mL)
- extractionthe aqueous phase is extracted with EtOAc (3×200 mL)
- dry with materialThe combined organic layers are dried over Na2SO4
- filtrationfiltered
- customevaporated under vacuum
Sources & evidence
- ORD record
- ord-15d08f53d3e4487f961b5e25e57b9959
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08455646B2
Reaction notes
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