Triethylamine → HCID 86617445, compound
Reaction equation
[CH2:1]([O:17][CH2:18][CH2:19][CH2:20][OH:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16].CCN(CC)CC.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([O:17][CH2:18][CH2:19][CH2:20][O:21][S:30]([CH3:29])(=[O:32])=[O:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To 7.1 g (23.7 mmol) of 31 was added 20 mL of DCM and 5.0 mL (36 mmol) of Et3N and the solution was cooled to 0° C. To this cooled solution was added dropwise 2.0 mL (26 mmol) of MsCl and a catalytic amount of DMAP. The reaction was stirred at room temperature overnight. The reaction mixture was then diluted with 50 mL of DCM and washed successively with saturated solution of aq. NaHCO3 (1×), water (1×) and brine (1×), dried over MgSO4 and the solvent was evaporated under reduced pressure. The crude product was then purified by combiflash using hexane/ethyl acetate as eluent to furnish 9 g of target product 32 in quantitative yield.
Workup
- washwashed successively with saturated solution of aq. NaHCO3 (1×), water (1×) and brine (1×)
- dry with materialdried over MgSO4
- customthe solvent was evaporated under reduced pressure
- customThe crude product was then purified by combiflash
Sources & evidence
- ORD record
- ord-9dbf40722b1c4c6eb1797d9792ad3894
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07749983B2
Reaction notes
Loading…