Reaction equation
[C:1]([CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15](=[O:23])[NH:16][CH2:17][CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:12][CH:13]=2)[C:8]([CH2:24][C:25]2[CH:34]=[CH:33][C:28]([C:29]([O:31]C)=[O:30])=[CH:27][C:26]=2[O:35][CH3:36])=[CH:7]1)(=[O:3])[NH2:2].CO.O1CCCC1.O.[OH-].[Li+]>O>[C:1]([CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15](=[O:23])[NH:16][CH2:17][CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:12][CH:13]=2)[C:8]([CH2:24][C:25]2[CH:34]=[CH:33][C:28]([C:29]([OH:31])=[O:30])=[CH:27][C:26]=2[O:35][CH3:36])=[CH:7]1)(=[O:3])[NH2:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of methyl 4-[1-(2-carbamoylethyl)-5-(N-cyclopentylmethylcarbamoyl)indol-3-ylmethyl]-3-methoxybenzoate (0.13 g) in a combination of methanol (2 ml), tetrahydrofuran (2 ml), and water (1 ml) was treated with lithium hydroxide monohydrate (0.07 g). The mixture was stirred for 12 hours and then concentrated to remove the organic solvents. The resultant aqueous solution was acidified with 10% (v/v) hydrochloric acid. The white precipitate which formed was collected by filtration, washed with water, and dried under vacuum to give the title compound (0.10 g, 79%) as a white powder, mp 129°-131° C.
Workup
- concentrationconcentrated
- customto remove the organic solvents
- customThe white precipitate which formed
- filtrationwas collected by filtration
- washwashed with water
- customdried under vacuum
Sources & evidence
- ORD record
- ord-0dbc6dc74e0441d38563e3cbb8354517
- Source dataset
- uspto-grants-1991_09
- Patent number
- US05049576
Linked notes
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