Methanol → Methyl 2-amino-4,4,4-trifluoro-3-(trifluoromethyl)butanoate
Reaction equation
[F:1][C:2]([F:14])([F:13])[CH:3]([C:9]([F:12])([F:11])[F:10])[CH:4]([C:6]([OH:8])=[O:7])[NH2:5].[Si](C=[N+]=[N-])(C)(C)[CH3:16].CO>C(Cl)Cl.CO.C(Cl)(Cl)Cl>[F:1][C:2]([F:13])([F:14])[CH:3]([C:9]([F:11])([F:10])[F:12])[CH:4]([C:6]([O:8][CH3:16])=[O:7])[NH2:5]Participants
6
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 4,4,4,4′,4′,4′-hexafluoro-dl-valine (2.5 g, 11.11 mmol) in CH2Cl2-MeOH (4:1, 25 mL) at 0° C. was added TMS-diazomethane (2.0 M in hexane, 45 mmol, 23 mL) dropwise. The resulting neon greenish solution was stirred for 19 hours at 25° C. After this time period, the reaction was complete by TLC (10% MeOH in chloroform). After concentration, the resulting residue of methyl 4,4,4,4′,4′,4′-hexafluoro-dl-valinate (2.35 g) was used directly in the next step without further purification. Mass Spectrum (−ESI): 238 [M−H]−.
Workup
- concentrationAfter concentration
- customthe resulting residue of methyl 4,4,4,4′,4′,4′-hexafluoro-dl-valinate (2.35 g) was used directly in the next step without further purification
Sources & evidence
- ORD record
- ord-66414d9efa104cbcb3b349b85d6b05f2
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07550629B2
Reaction notes
Loading…