Potassium Hydroxide → 2-((Tert-butoxycarbonyl)(2-(tert-butyldisulfanyl)ethyl)amino)acetic acid
Reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:15][CH2:16][S:17][S:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:9][C:10]([O:12]CC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>CO>[C:1]([O:5][C:6]([N:8]([CH2:15][CH2:16][S:17][S:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
4
Procedure
Ethyl 2-((tert-butoxycarbonyl)(2-(tert-butyldisulfanyl)ethyl)amino)acetate (Compound 6e-A, 320 mg, 0.91 mmol) was dissolved in methanol (80 ml), an aqueous potassium hydroxide solution (0.18 mol/l, 30.3 ml) was added and the mixture was stirred at room temperature for 2 hours. Methanol in the reaction solution was removed by concentration under reduced pressure, and the aqueous layer was washed with diethyl ether and then adjusted to pH 3 with a 1 mol/1 aqueous hydrochloric acid solution. The aqueous layer was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford the title compound (268.1 mg, 91%).
Workup
- customMethanol in the reaction solution was removed by concentration under reduced pressure
- washthe aqueous layer was washed with diethyl ether
- extractionThe aqueous layer was extracted with ethyl acetate
- dry with materialthe organic layer was dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-b629cff421b84165912c64a668e31c51
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409952B2
Reaction notes
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