Dichloromethane → 5-(2-Chlorobenzyl)-4-methoxymethyl-9-tosyl-beta-carboline-3-carboxylic acid ethyl ester
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:12]([O:14][C:15]([C:17]1[N:18]=[CH:19][C:20]2[NH:21][C:22]3[C:27]([C:28]=2[C:29]=1[CH2:30][O:31][CH3:32])=[C:26]([CH2:33][C:34]1C=[CH:38][C:37](Cl)=[CH:36][CH:35]=1)[CH:25]=[CH:24][CH:23]=3)=[O:16])[CH3:13].CN(C1C=CC=CN=1)C.C(N(CC)CC)C.Cl[CH2:58][Cl:59]>>[CH2:12]([O:14][C:15]([C:17]1[N:18]=[CH:19][C:20]2[N:21]([S:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)(=[O:10])=[O:9])[C:22]3[C:27]([C:28]=2[C:29]=1[CH2:30][O:31][CH3:32])=[C:26]([CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:58]=1[Cl:59])[CH:25]=[CH:24][CH:23]=3)=[O:16])[CH3:13]Participants
Reactant 5
Product 1
Procedure
0.744 g (0.0039 mol) of p-toluenesulfochloride is added under ice cooling to a solution of 1.2 g (0.0029 mol) of 5-(4-chlorobenzyl)-4-methoxymethyl-β-carboline-3-carboxylic acid ethyl ester, 0.16 g (0.0013 mol) of dimethylaminopyridine and 0.54 ml (0.0039 mol) of triethylamine in 120 ml of dichloromethane. The reaction mixture is stirred for another 15 minutes under ice cooling and then for 2 hours at room temperature. Then it is diluted with dichloromethane, washed with water, dried and concentrated by evaporation. The evaporation residue is crystallized under trituration with ether. The yield is 1.36 g (82% of theory) of 5-(2-chlorobenzyl)-4-methoxymethyl-9-tosyl-β-carboline-3-carboxylic acid ethyl ester, melting point 140°-142° C.
Workup
- waitfor 2 hours at room temperature
- washwashed with water
- customdried
- concentrationconcentrated by evaporation
- customThe evaporation residue is crystallized under trituration with ether
Sources & evidence
- ORD record
- ord-abc7e3116cf34163aa8095bd0ae078c7
- Source dataset
- uspto-grants-1996_04
- Patent number
- US05506234
Reaction notes
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