Water → (2R)-2-[(tert-butoxycarbonyl)(methyl)amino]-3-[4-(trifluoromethyl)phenyl]-propanoic acid
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:26]I.O>C1COCC1>[C:1]([O:5][C:6]([N:8]([CH3:26])[C@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (2R)-2-[(tert-butoxycarbonyl)amino]-3-[4-(trifluoromethyl)phenyl]propanoic acid XII (1 g, 3 mmol) in dry THF (10 mL) was added sodium hydride (60% suspension in mineral oil) (0.72 g, 18 mmol; 6 eq. of pure NaH) in portions. Methyl iodide (1.12 mL, 18 mmol) was then added and the mixture was stirred at r.t. for 3 days. The mixture was then treated with water before removing the THF under reduced pressure. The aqueous phase was acidified and extracted EtOAc (2×). The combined EtOAc was washed with sodium thiosulfate, dried and evaporated under reduced pressure. The residue was crystallized to produce (2R)-2-[(tert-butoxycarbonyl) (methyl)amino]-3-[4-(trifluoromethyl)phenyl]-propanoic acid L (0.73 g, 2 mmol, 70% yield).
Workup
- custombefore removing the THF under reduced pressure
- extractionextracted EtOAc (2×)
- washThe combined EtOAc was washed with sodium thiosulfate
- customdried
- customevaporated under reduced pressure
- customThe residue was crystallized
Sources & evidence
- ORD record
- ord-b78a7e6933304ccb91c37929066e7ba5
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268865B2
Reaction notes
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