Triethylamine → HCID 13857264, compound
Reaction equation
[C:1]([NH:8][C@@H:9]([CH2:17][OH:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(N(CC)CC)C>C(Cl)Cl>[CH3:19][S:20]([O:18][CH2:17][C@@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2])(=[O:22])=[O:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A cold solution (0° C.) of N-Boc-D-phenylalaninol (0.53 g, 2.09 mmol) in anhydrous methylene chloride (20 mL) was treated sequentially with methanesulfonyl chloride (360 mg, 3.14 mmol) and triethylamine (0.32 g, 3.14 mmol). The reaction was stirred at 0° C. for 2 hr, quenched with 1M hydrochloric acid (2×25 mL) and extracted with methylene chloride. The combined extract was washed with saturated sodium bicarbonate (1×25 mL), and brine (1×25 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate adsorbed onto silica gel and applied to a column prepacked with silica gel. The title compound was eluted from the column with hexane:ethyl acetate (60:40, v:v) to furnish titled compound (352 mg) as a white solid.
Workup
- customquenched with 1M hydrochloric acid (2×25 mL)
- extractionextracted with methylene chloride
- extractionThe combined extract
- washwas washed with saturated sodium bicarbonate (1×25 mL), and brine (1×25 mL)
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- filtrationfiltered
- washThe title compound was eluted from the column with hexane:ethyl acetate (60:40, v:v)
Sources & evidence
- ORD record
- ord-b999ffc542db4d0f933399ae52923cf2
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06114310
Reaction notes
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