Hydrochloric Acid → 3-((8-((2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)methyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

HRID 1751027Notes

Reaction equation

HRID 1751027 reaction equation
[O:1]1[CH:6]([CH2:7][N:8]2[CH2:38][CH2:37][C:11]3([N:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:14][N:13]([CH2:22][C:23]4[CH:24]=[C:25]([CH:33]=[CH:34][CH:35]=4)[C:26]([O:28]C(C)(C)C)=[O:27])[C:12]3=[O:36])[CH2:10][CH2:9]2)[CH2:5][O:4][C:3]2[CH:39]=[CH:40][CH:41]=[CH:42][C:2]1=2.Cl>O1CCOCC1>[O:1]1[CH:6]([CH2:7][N:8]2[CH2:9][CH2:10][C:11]3([N:15]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH2:14][N:13]([CH2:22][C:23]4[CH:24]=[C:25]([CH:33]=[CH:34][CH:35]=4)[C:26]([OH:28])=[O:27])[C:12]3=[O:36])[CH2:37][CH2:38]2)[CH2:5][O:4][C:3]2[CH:39]=[CH:40][CH:41]=[CH:42][C:2]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58046715Tert-butyl 3-((8-((2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Product 1

HCID 580466653-((8-((2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)methyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl 3-((8-((2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.17 g, 0.3 mmol) was added 4M solution of HCl in dioxane (3 mL). After stirring at room temperature for 4 hours, the reaction mixture was concentrated in vacuo and lyophilized in acetonitrile/water (1:1) to obtain the title compound as a hydrochloride salt (0.16 g, 99%); 1H NMR (DMSO-d6): δ 1.96 (d, 2H, J=14 Hz), 2.91-3.02 (m, 2H), 3.45-3.71 (m, 6H), 4.03-4.08 (m, 1H), 4.36 (d, 1H, J=9.2 Hz), 4.61-4.66 (m, 4H), 4.92 (br, 1H), 6.81-6.97 (m, 5H), 7.04 (d, 2H, J=8 Hz), 7.24 (t, 2H, J=8.4 Hz), 7.49-7.59 (m, 2H), 8.89 (d, 2H, J=8.8 Hz), 10.83 (br, 1H), 13.04 (br, 1H); MS for C30H31N3O5 m/z 513.99 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-80ad04c6f47c458e8928283418a81b45
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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