Methanol → 3-((8-(4-(4-Fluorophenyl)-4-oxobutyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

HRID 1751000Notes

Reaction equation

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

Participants

Conditions

Temperature: 35 °C

Procedure

A solution of methyl 3-((8-(4-(4-fluorophenyl)-4-oxobutyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (450 mg, 0.828 mmol, 1 equiv) and lithium hydroxide (34.7 mg, 1.656 mmol, 2.0 equiv) in a 3:1 mixture of methanol and water (5 ml t/v) was stirred at 35° C. for 24 hrs. The reaction was concentrated in vacuo and purified using preparatory high performance liquid chromatography. The combined pure fractions were lyophilized to afford the acetate salt of the title compound as a white solid (100 mg, 25%); 1H NMR (400 MHz, DMSO-d6): δ 1.59 (d, 2H, J=13.6 Hz), 1.84 (t, 2H, J=7.2 and 6.8 Hz); 2.45-2.46 (m, 4H); 2.72-2.78 (m, 4H); 3.05 (t, 2H, J=6.8 and 7.2 Hz); 4.57 (s, 2H); 4.60 (s, 2H); 6.72-6.78 (m, 3H); 7.12-7.16 (m, 2H); 7.32-7.36 (m, 2H); 7.47-7.53 (m, 2H); 7.86-7.88 (m, 2H); 8.04-8.08 (m, 2H); 10.82 (s, 1H); 12.9 (bs, 1H); MS for C31H32FN3O4 m/z 529.99 (M+H)+.

Workup

concentrationThe reaction was concentrated in vacuo
custompurified

Sources & evidence

ORD record: ord-bbe82d6723894ffba6a342ebe715fef9
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156840B2

Reaction notes

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