Triethylamine → N-Methylsulfonyl-4-{3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzamide
Reaction equation
[CH3:1][S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[OH:8][C:9]1([CH2:15][CH2:16][N:17]2[C:21](=[O:22])[CH2:20][S:19][CH:18]2[CH2:23][CH2:24][CH2:25][C:26]2[CH:34]=[CH:33][C:29](C(O)=O)=[CH:28][CH:27]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C(N(CC)CC)C>C(#N)C>[CH3:1][S:2]([NH:5][C:6](=[O:7])[C:29]1[CH:28]=[CH:27][C:26]([CH2:25][CH2:24][CH2:23][CH:18]2[N:17]([CH2:16][CH2:15][C:9]3([OH:8])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)[C:21](=[O:22])[CH2:20][S:19]2)=[CH:34][CH:33]=1)(=[O:4])=[O:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of methanesulfonylisocyanate (1.33 g., 0.011 mole) in acetonitrile (10 ml.) is added dropwise during 10 minutes to a solution of 4-{3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic acid (3.9 g., 0.01 mole) and triethylamine (1.0 g., 0.01 mole) in acetonitrile (30 ml.). The resulting solution is stored at 25° C. for 4 hours and then evaporated at reduced pressure. The residue is treated with water. The crude product is extracted into chloroform and purified by chromatography on a silica gel column with elution by 4% methanol in chloroform.
Workup
- customevaporated at reduced pressure
- additionThe residue is treated with water
- extractionThe crude product is extracted into chloroform
- custompurified by chromatography on a silica gel column with elution by 4% methanol in chloroform
Sources & evidence
- ORD record
- ord-b4620ef5fe9b4974ba8417c99a6c0a7f
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04225609
Reaction notes
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