Ammonia → benzyl 3-aminosulfonyl-2(R)-methylpropionate
Reaction equation
Cl[S:2]([CH2:5][C@H:6]([CH3:17])[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])(=[O:4])=[O:3].[NH3:18]>C(Cl)Cl.C(OCC)(=O)C>[NH2:18][S:2]([CH2:5][C@H:6]([CH3:17])[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])(=[O:4])=[O:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
A 100 mL round bottom flask equipped with magnetic stir bar was charged with 1.22 g of benzyl 3-chlorosulfonyl-2(R)-methylpropionate in 15 mL CH2Cl2 and cooled to −78° C. To this solution was added to 10 mL of liquid ammonia at −78° C. After 20 minutes the reaction was warmed to room temperature, concentrated in vacuo to afford a white solid. The solid was slurried in ethyl acetate, filtered to remove inorganic salts and concentrated in vacuo to afford 1.08 g of benzyl 3-aminosulfonyl-2(R)-methylpropionate as a clear yellow oil. The crude product was used without further purification. Part B: 3-aminosulfonyl-2(R)-methylpropionic acid A 100 mL Fisher/Porter vessel was charged with 1.1 g of crude benzyl 3-aminosulfonyl-2(R)-methylpropionate in 35 mL MeOH and a catalytic amount of 10% Pd—C. The mixture was hydrogenated at 50 psi for 24 hours, filtered through Celite and concentrated in vacuo to yield 700 mg of 3-aminosulfonyl-2(R)-methylpropionic acid as a clear oil. The crude acid was used without further purification.
Workup
- customA 100 mL round bottom flask equipped with magnetic stir bar
- temperatureAfter 20 minutes the reaction was warmed to room temperature
- concentrationconcentrated in vacuo
- customto afford a white solid
- filtrationfiltered
- customto remove inorganic salts
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-961f9028601d4c8d9b948a5c12852a84
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07297793B2
Reaction notes
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