Water → Tert-Butyl (2-(methylthio)ethyl)carbamate
Reaction equation
Cl.[CH3:2][S:3][CH2:4][CH2:5][NH2:6].[CH2:7](N(CC)CC)C.[OH2:14].[C:15](OCC)(=[O:17])C.O1[CH2:25][CH2:24][CH2:23]C1>>[CH3:2][S:3][CH2:4][CH2:5][NH:6][C:15](=[O:17])[O:14][C:24]([CH3:23])([CH3:25])[CH3:7]Participants
6
Procedure
In a dried reaction flask, 2-(methylthio)ethylamine hydrochloride (6.382 g, 50.0 mmol) and TEA (triethylamine) (13.9 mL, 100 mmol) were dissolved in tetrahydrofuran (63.3 mL). To the mixture was added dropwise Boc2O(di-tert-butyl dicarbonate) (12.3 g, 56.4 mmol) dissolved in tetrahydrofuran (10 mL) under an ice-salt bath. The mixture was stirred at room temperature for 21 hr. Water and ethyl acetate were added. The mixture was extracted with ethyl acetate. The combined organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated to produce a crude colorless oil (11.752 g).
Workup
- extractionThe mixture was extracted with ethyl acetate
- washThe combined organic phase was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d3523f4989dd440b8145d046539256e9
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946279B2
Reaction notes
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