Triethylamine → 3-(5-ethanesulfonylamino-1H-indol-3-yl)propyl methanesulfonate
Reaction equation
[CH2:1]([S:3]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH2:16][CH2:17][CH2:18][OH:19])(=[O:5])=[O:4])[CH3:2].C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29].C([O-])(O)=O.[Na+]>C1COCC1.C(OCC)(=O)C>[CH3:27][S:28]([O:19][CH2:18][CH2:17][CH2:16][C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([NH:6][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH:8]=2)[NH:12][CH:11]=1)(=[O:30])=[O:29]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3-(5-ethanesulfonylamino-1H-indol-3-yl)propanol (0.59 g, 2.1 mmol) in 20 mL of THF at 0° C. was added triethylamine (0.58 mL, 4.2 mmol) followed by the dropwise addition of methanesulfonyl chloride (0.24 mL, 3.1 mmol). The reaction was stirred for 30 minutes at 0° C. The reaction was poured into a mixture of saturated NaHCO3 and ethyl acetate. The organic phase was separated and the aqueous phase reextracted with three portions of ethyl acetate. The combined organic layers were washed with a saturated NaCl solution, dried over anhydrous K2CO3, filtered, and concentrated in vacuo to yield 3-(5-ethanesulfonylamino-1H-indol-3-yl)propyl methanesulfonate (0.75 g, >99%) which was used without further purification.
Workup
- customThe organic phase was separated
- washThe combined organic layers were washed with a saturated NaCl solution
- dry with materialdried over anhydrous K2CO3
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-72a8885d43f744ac8f1ae7b9b47dbe36
- Source dataset
- uspto-grants-1994_04
- Patent number
- US05300506
Reaction notes
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