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)Cl>C(Cl)Cl.CO>[NH2:5][CH:4]([CH:3]([C:9]([F:11])([F:10])[F:12])[C:2]([F:13])([F:14])[F:1])[C:6]([O:8][CH3:16])=[O:7]Participants
6
Conditions
- Temperature
- 25 °C
Procedure
A solution of 4,4,4,4′,4′,4′-hexafluoro-dl-valine (2.00 g, 8.89 mmol) in CH2Cl2:MeOH (4:1, 50 mL) was stirred under nitrogen at 0° C. TMS diazomethane (5.33 mL, 2.0 M in hexane) was added dropwise and the resulting solution stirred for 4 hours at 25° C. After this time period, the reaction was complete by TLC (10% MeOH: chloroform). After concentration, the resulting residue (2.12 g, 99%) was used directly in the next reaction without further purification.
Workup
- concentrationAfter concentration
- customthe resulting residue (2.12 g, 99%) was used directly in the next reaction without further purification
Sources & evidence
- ORD record
- ord-6d4e520eb4524a639041bd5c3e2ca661
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07550629B2
Reaction notes
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