Potassium Bromide → 2-(((Tert-butoxy)carbonyl)amino)-3-methoxy-3-methylbutanoic acid
Reaction equation
[OH:1][CH2:2][CH:3]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:4]([O:7][CH3:8])([CH3:6])[CH3:5].C(=O)([O-])[OH:18].[Na+].[Br-].[K+].Cl[O-].[Na+]>CC(C)=O>[C:12]([O:11][C:10]([NH:9][CH:3]([C:4]([O:7][CH3:8])([CH3:5])[CH3:6])[C:2]([OH:18])=[O:1])=[O:16])([CH3:15])([CH3:14])[CH3:13]Participants
6
Procedure
tert-Butyl 1-(hydroxymethyl)-2-methoxy-2-methylpropylcarbamate (0.23 g) obtained in Example 73b) was dissolved in acetone (8 ml) and a 5% aqueous sodium hydrogen carbonate solution (2.7 ml). Potassium bromide (0.01 g), 2,2,6,6-tetramethyl-1-piperidinyloxy (0.17 g) and an aqueous sodium hypochlorite solution (1.7 ml) were added thereto, and mixed at 0° C. for 50 minutes. Acetone was distilled off under reduced pressure, and the residue was diluted with water, washed with diethyl ether, acidified with 1 N hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound as a pale yellow oil (0.20 g, 82%).
Workup
- additionmixed at 0° C. for 50 minutes
- distillationAcetone was distilled off under reduced pressure
- additionthe residue was diluted with water
- washwashed with diethyl ether
- extractionextracted with ethyl acetate
- dry with materialThe extract was dried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-40be0bdfa631458e8bc502d9b0aeeb8a
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820673B2
Reaction notes
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