Lithium hydroxide, monohydrate → 3-(4-Oxo-8-(4-oxo-4-phenylbutyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)benzoic acid

HRID 2363054Notes

Reaction equation

[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][C:15](=[O:22])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:8][CH2:7]2)[N:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:4][N:3]1[C:29]1[CH:30]=[C:31]([CH:36]=[CH:37][CH:38]=1)[C:32]([O:34]C)=[O:33].O.[OH-].[Li+].Cl.O1CCOCC1>CO.O>[O:1]=[C:2]1[C:6]2([CH2:7][CH2:8][N:9]([CH2:12][CH2:13][CH2:14][C:15](=[O:22])[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:10][CH2:11]2)[N:5]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:4][N:3]1[C:29]1[CH:30]=[C:31]([CH:36]=[CH:37][CH:38]=1)[C:32]([OH:34])=[O:33]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of methyl 3-(4-oxo-8-(4-oxo-4-phenylbutyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)benzoate (0.08 g, 0.16 mmol) in methanol (3 mL) was added lithium hydroxide monohydrate (0.013 g, 0.32 mmol) in water (1 mL). After stirring at 55° C. for 18 h, the reaction mixture was concentrated in vacuo, isolated by preparatory TLC (10% methanol/dichloromethane/0.1% acetic acid) and lyophilized with 4M HCl/dioxane (0.5 mL) to obtain the title compound as a hydrochloride salt (0.011 g, 13%); 1H NMR (DMSO-d6): δ 2.07-2.16 (m, 4H), 2.91 (br, 2H), 3.21-3.24 (m, 4H), 3.56-3.62 (m, 4H), 5.25 (s, 2H), 6.90 (t, 1H, J=7.2 Hz), 7.24-7.34 (m, 4H), 7.53-7.68 (m, 4H), 7.81 (d, 1H, J=7.6 Hz), 7.92 (dd, 1H, J=8 and 1.6 Hz), 8.00 (d, 2H, J=8 Hz), 8.69 (s, 1H), 10.29 (br, 1H), 13.18 (br, 1H); MS for C30H31N3O4 m/z 498 (M+H)+.

Workup

concentrationthe reaction mixture was concentrated in vacuo
customisolated by preparatory TLC (10% methanol/dichloromethane/0.1% acetic acid)

Sources & evidence

ORD record: ord-9ea7d56d4fe4441097e0515136bc1e21
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691836B2

Reaction notes

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