Triethylamine → (S)-2-amino-3-(tert-butyldisulfanyl)propanoic acid
Reaction equation
O.Cl.[NH2:3][C@H:4]([CH2:8][SH:9])[C:5]([OH:7])=[O:6].CS(=O)([S:13][C:14]([CH3:17])([CH3:16])[CH3:15])=O.C(N(CC)CC)C>CO.O1CCCC1>[NH2:3][C@H:4]([CH2:8][S:9][S:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:5]([OH:7])=[O:6]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of (S)-2-amino-3-mercaptopropanoic acid hydrochloride hydrate (1.00 g, 5.69 mmol) in methanol (5.1 mL) was mixed with a solution of the prepared S-tert-butyl methanesulfonothioate (Compound SP684, 1.05 g, 6.26 mmol) in tetrahydrofuran (2.0 mL) and triethylamine (2.38 mL, 17.1 mmol) with stirring at 0° C., and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was purified by reverse-phase silica gel column chromatography (0.1% aqueous formic acid solution/0.1% formic acid-acetonitrile solution) to afford (S)-2-amino-3-(tert-butyldisulfanyl)propanoic acid (H-D-Cys(StBu)-OH) (Compound SP641) (620 mg, 2.96 mmol, 52%).
Workup
- stirringthe reaction mixture was stirred at room temperature for 3 hours
- customThe reaction mixture was purified by reverse-phase silica gel column chromatography (0.1% aqueous formic acid solution/0.1% formic acid-acetonitrile solution)
Sources & evidence
- ORD record
- ord-6f58043f8ebf48b2ad49b444892abbcb
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409952B2
Reaction notes
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