2-Chlorobenzoyl chloride → (R)-Methyl 3-(2-chloro-N-isobutylbenzamido)-2,3-dihydro-1H-indene-5-carboxylate
Reaction equation
[CH2:1]([NH:5][C@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[CH2:8][CH2:7]1)[CH:2]([CH3:4])[CH3:3].[Cl:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23]>ClCCl>[Cl:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([N:5]([C@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[CH2:8][CH2:7]1)[CH2:1][CH:2]([CH3:4])[CH3:3])=[O:23]Participants
4
Procedure
TEA (1.4 ml, 10.1 mmol, 2.5 eq) was added dropwise at 0° C. to a solution of (R)-methyl 3-(isobutylamino)-2,3-dihydro-1H-indene-5-carboxylate (A-08) (1.0 g, 4.04 mmol, 1 eq) in dichloromethane (25 ml), and stirring was carried out for 15 min. Then 2-chlorobenzoic acid chloride (0.61 ml, 4.858 mmol, 1.2 eq) was added at that temperature, and stirring was carried out for 1 h at RT. After monitoring by thin-layer chromatography, the reaction mixture was diluted with dichloromethane (75 ml), washed with water and sat. NaCl solution (in each case 50 ml), dried over sodium sulfate and purified by column chromatography (silica gel, 2% MeOH in dichloromethane). Yield: 51% (800 mg, 2.078 mmol).
Workup
- stirringstirring
- waitwas carried out for 1 h at RT
- washwashed with water and sat. NaCl solution (in each case 50 ml),
- dry with materialdried over sodium sulfate
- custompurified by column chromatography (silica gel, 2% MeOH in dichloromethane)
Sources & evidence
- ORD record
- ord-798ced0fcfe64aa1aa334c91fc8d2829
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680159B2
Reaction notes
Loading…