Sodium Hydroxide → HCID 9935773, compound

HRID 396709Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of ethyl (R/S) 3-(1-{[3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetyl}-2,3-dihydro-1H-indol-5-yl)-butyrate [2.8 g, Reference Example 4(a)] in methanol (about 150 ml) was treated with aqueous sodium hydroxide solution (15 ml, 1M). The mixture was warmed at about 50° C. for 3 hours, then treated with a further aliquot of aqueous sodium hydroxide solution (7.5 ml). After a further 2-3 hours at 50° C. TLC analysis indicated complete reaction. The bulk of the methanol was removed by evaporation and the residue was diluted with hydrochloric acid (about 200 ml, 1M). The resulting mixture was stirred for about 30 minutes, then the solid was collected by filtration, washed with water, and dried to give the title compound (2.3 g) as a very light orange powder. LC-MS: RT=3.84 minutes (100% total area by ELS); MS (ES+) 502 (MH+), 524 (MNa+).

Workup

customreaction
customThe bulk of the methanol was removed by evaporation
additionthe residue was diluted with hydrochloric acid (about 200 ml, 1M)
filtrationthe solid was collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-eebb9ce687e74bb9be2b204b168282a6
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608084B1

Reaction notes

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