Citric Acid → 3-[(3-{[3-(6-{[(2E)-1-(4-methoxyphenyl)-2-methyl-1-phenylpenta-2,4-dienyl]amino}hexanoyl)pyrrolo[4,5-e]indolin-7-yl]carbonyl}pyrrolo[4,5-e]indolin-7-yl)carbonyl]pyrrolo[4,5-e]indoline-7-carboxylic acid

HRID 1593537Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([N:29]2[C:40]3[C:32](=[C:33]4[C:37](=[CH:38][CH:39]=3)[NH:36][CH:35]([C:41]([N:43]3[C:54]5[C:46](=[C:47]6[C:51](=[CH:52][CH:53]=5)[NH:50][CH:49]([C:55]([N:57]5[C:68]7[C:60](=[C:61]8[C:65](=[CH:66][CH:67]=7)[NH:64][CH:63]([C:69]([O:71]C)=[O:70])[CH2:62]8)[CH:59]=[CH:58]5)=[O:56])[CH2:48]6)[CH:45]=[CH:44]3)=[O:42])[CH2:34]4)[CH:31]=[CH:30]2)=[O:28])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)/[C:10](/[CH3:14])=[CH:11]/[CH:12]=[CH2:13])=[CH:5][CH:4]=1.CO.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([N:29]2[C:40]3[C:32](=[C:33]4[C:37](=[CH:38][CH:39]=3)[NH:36][CH:35]([C:41]([N:43]3[C:54]5[C:46](=[C:47]6[C:51](=[CH:52][CH:53]=5)[NH:50][CH:49]([C:55]([N:57]5[C:68]7[C:60](=[C:61]8[C:65](=[CH:66][CH:67]=7)[NH:64][CH:63]([C:69]([OH:71])=[O:70])[CH2:62]8)[CH:59]=[CH:58]5)=[O:56])[CH2:48]6)[CH:45]=[CH:44]3)=[O:42])[CH2:34]4)[CH:31]=[CH:30]2)=[O:28])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)/[C:10](/[CH3:14])=[CH:11]/[CH:12]=[CH2:13])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A suspension of 10 (270 mg, 0.28 mmol) in a mixture of THF (6 ml), MeOH (4 ml) and 4M LiOH (2 ml) was stirred at 55° C. for 30 h. The reaction was cooled and neutralized to pH 6 with cold 10% citric acid. Insoluble material was collected by filtration and washed with water, MeOH and ether. Drying under vacuum afforded 160 mg (60%) of the title compound 11. By HPLC analysis this product contained ˜5% of unreacted 10. The crude acid was used in the next step without additional purification.

Workup

temperatureThe reaction was cooled
filtrationInsoluble material was collected by filtration
washwashed with water, MeOH and ether
customDrying under vacuum

Sources & evidence

ORD record: ord-e8e231d27e204912a6fc946214ec2db1
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07297495B2

Reaction notes

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