Triethylamine → HCID 76488224, compound
Reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].NCCCCS([NH:17][CH2:18][CH:19]1[CH2:23][CH2:22][CH2:21][N:20]1[C:24](=[O:41])[CH:25]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=O)=O.C(N(CC)CC)C>ClCCl>[Br:1][CH2:2][CH2:3][CH2:4][S:5]([NH:17][CH2:18][CH:19]1[CH2:23][CH2:22][CH2:21][N:20]1[C:24](=[O:41])[CH:25]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:37])([CH3:39])[CH3:38])[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)(=[O:7])=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
A solution of Part A 3-bromopropyl sulfonyl chloride (1.06 g, 4.8 mmol) in dichloromethane (5 mL) was added dropwise to a cooled (-10° C.) stirred solution of Example 6a, Part B amine (1.05 g, 3.02 mmol) and triethyl amine (1.44 mL, 9.6 mmol) in dichloromethane (15 mL). After a few minutes, a precipitate formed. The suspension was stirred at -10° C. for 2.5 hours, diluted with dichloromethane (35 mL) and washed with 1N HCl solution (2×15 mL). The dichloromethane solution was dried (MgSO4), filtered and the solvent was removed in vacuo. The crude oil was purified on silica gel (Merck, 150 mL) eluting with 50% ethyl acetate in hexane to give title compound as a white foam (1.160 g, 72%).
Workup
- waitAfter a few minutes
- customa precipitate formed
- washwashed with 1N HCl solution (2×15 mL)
- dry with materialThe dichloromethane solution was dried (MgSO4)
- filtrationfiltered
- customthe solvent was removed in vacuo
- customThe crude oil was purified on silica gel (Merck, 150 mL)
- washeluting with 50% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-eeedfc74393742b89ba7008c64e57f6a
- Source dataset
- uspto-grants-1998_04
- Patent number
- US05741792
Reaction notes
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