Hydrochloric Acid → 2-Methyl-2-(4-((4-oxo-8-(3-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenoxy)propanoic acid

HRID 1751048Notes

Reaction equation

HRID 1751048 reaction equation
[CH3:1][C:2]([O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]2[C:23](=[O:24])[C:22]3([CH2:29][CH2:28][N:27]([CH2:30][CH2:31][CH2:32][N:33]4[C:37]5[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=5[NH:35][C:34]4=[O:42])[CH2:26][CH2:25]3)[N:21]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:20]2)=[CH:14][CH:13]=1)([CH3:10])[C:3]([O:5]C(C)(C)C)=[O:4].Cl>O1CCOCC1>[CH3:10][C:2]([O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]2[C:23](=[O:24])[C:22]3([CH2:29][CH2:28][N:27]([CH2:30][CH2:31][CH2:32][N:33]4[C:37]5[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=5[NH:35][C:34]4=[O:42])[CH2:26][CH2:25]3)[N:21]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:20]2)=[CH:14][CH:13]=1)([CH3:1])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58046641tert-butyl 2-methyl-2-(4-((4-oxo-8-(3-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenoxy)propanoate

Product 1

HCID 580466512-Methyl-2-(4-((4-oxo-8-(3-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenoxy)propanoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl 2-methyl-2-(4-((4-oxo-8-(3-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenoxy)propanoate (0.2 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 (0.19 g, 99%); 1H NMR (DMSO-d6): δ 1.49 (s, 6H), 1.90 (d, 2H, J=14.4 Hz), 2.12-2.15 (m, 2H), 2.87-2.93 (m, 2H), 3.19-3.22 (m, 2H), 3.44-3.72 (m, 4H), 3.90 (t, 2H, J=6.4 Hz), 4.48 (s, 2H), 4.60 (s, 2H), 6.77-6.81 (m, 3H), 6.97-7.05 (m, 5H), 7.19-7.23 (m, 5H), 10.39 (br, 1H), 10.90 (s, 1H), 13.01 (br, 1H); MS for C34H39N5O5 m/z 598.21 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-fbb5f9e0b3014315bfbc124e9e78ba4b
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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