Lithium Hydroxide → 3-(6-{[1-(4-Methoxyphenyl)-2-methylene-1-phenylbut-3-enyl]amino}hexanoyl)pyrrolo[4,5-e]indoline-7-carboxylic acid

HRID 992908Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([N:28]2[C:39]3[C:31](=[C:32]4[C:36](=[CH:37][CH:38]=3)[NH:35][CH:34]([C:40]([O:42]C)=[O:41])[CH2:33]4)[CH:30]=[CH:29]2)=[O:27])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10](=[CH2:13])[CH:11]=[CH2:12])=[CH:5][CH:4]=1.C1COCC1.[Li+].[OH-]>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([N:28]2[C:39]3[C:31](=[C:32]4[C:36](=[CH:37][CH:38]=3)[NH:35][CH:34]([C:40]([OH:42])=[O:41])[CH2:33]4)[CH:30]=[CH:29]2)=[O:27])([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:10](=[CH2:13])[CH:11]=[CH2:12])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 8 (0.47 g, 0.78 mmol), THF (9 ml), MeOH (6 ml) and 4M LiOH (3 ml) was stirred at 55° C. for 1 h. The resultant solution was cooled to give a white precipitate, the Li salt of the product. The solid was triturated with a small amount of cold 10% citric acid and filtered off. Washing with water and drying under vacuum gave 0.43 g (94%) of 9 as a white solid.

Workup

customto give a white precipitate
customThe solid was triturated with a small amount of cold 10% citric acid
filtrationfiltered off
washWashing with water
customdrying under vacuum

Sources & evidence

ORD record: ord-13c4e51cb35c4eeab597c1b76885ec8a
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06472153B1

Reaction notes

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