Hydrochloric Acid → HCID 68846810, compound

HRID 1453360Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 1-cyclohexyl-3-(3-oxo-3-(4-(2-oxopyrrolidin-1-yl)piperidin-1-yl)propyl)-2-phenyl-3H-indene-5-carboxylic acid, methyl ester (460 mg, 0.1 mmol), in THF (1 mL) and MeOH (1 mL) was added 1M NaOH (0.16 mL, 0.16 mmol). The reaction mixture was heated in a sealed tube at 70° C. for 4 h. 1M NaOH (0.2 mL, 0.2 mmol) was added and heated for 5 h more. 1N HCl (0.5 mL) was added and the volatiles were removed in vacuo. A precipitate formed and it was collected by filtration and dried at open air to afford 1-cyclohexyl-3-(3-oxo-3-(4-(2-oxopyrrolidin-1-yl)piperidin-1-yl)propyl)-2-phenyl-3H-indene-5-carboxylic acid as a pale yellow solid. LCMS: m/e 552 (M+H)+, ret time 2.10 min, column A, 2 minute gradient.

Workup

temperatureheated for 5 h more
customthe volatiles were removed in vacuo
customA precipitate formed
filtrationit was collected by filtration
customdried at open air

Sources & evidence

ORD record: ord-4c7dad6e91574db288d9acb37d8512d0
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473688B2

Reaction notes

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