tert-butyl 3-((8-(3-(3-(3-methoxy-3-oxopropyl)-1H-indol-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate → 3-((8-(3-(3-(3-methoxy-3-oxopropyl)-1H-indol-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

HRID 1751062Notes

Reaction equation

HRID 1751062 reaction equation
[CH3:1][O:2][C:3](=[O:49])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:15][CH2:16][CH2:17][N:18]2[CH2:48][CH2:47][C:21]3([N:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:24][N:23]([CH2:32][C:33]4[CH:34]=[C:35]([CH:43]=[CH:44][CH:45]=4)[C:36]([O:38]C(C)(C)C)=[O:37])[C:22]3=[O:46])[CH2:20][CH2:19]2)[CH:7]=1>Cl.O1CCOCC1>[CH3:1][O:2][C:3](=[O:49])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:15][CH2:16][CH2:17][N:18]2[CH2:48][CH2:47][C:21]3([N:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:24][N:23]([CH2:32][C:33]4[CH:34]=[C:35]([CH:43]=[CH:44][CH:45]=4)[C:36]([OH:38])=[O:37])[C:22]3=[O:46])[CH2:20][CH2:19]2)[CH:7]=1

Participants

4

Reactant 1

HCID 58046653tert-butyl 3-((8-(3-(3-(3-methoxy-3-oxopropyl)-1H-indol-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Product 1

HCID 580467363-((8-(3-(3-(3-methoxy-3-oxopropyl)-1H-indol-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acidYield 35.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 3-((8-(3-(3-(3-methoxy-3-oxopropyl)-1H-indol-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (400 mg, 0.637 mmol, 1 equiv) in 4M hydrogen chloride solution in dioxane was stirred at ambient temperature for 3 h. The mixture was concentrated in vacuo and the crude residue was purified using preparatory high performance liquid chromatography to afford the acetate salt of the title compound as a white solid (130 mg, 35.7%); 1H NMR (400 MHz, DMSO-d6): δ 1.62 (d, 2H, J=13.2 Hz); 1.89-1.93 (m, 2H); 2.27 (t, 2H, J=6.8 Hz); 2.59-2.72 (m, 8H); 2.95 (t, 2H, J=7.6 and 8 Hz); 3.57 (s, 3H); 4.19 (t, 2H, J=6.8 and 6.4 Hz); 4.59 (s, 2H); 4.61 (s, 2H); 6.76 (t, 1H, J=7.2 Hz); 6.87 (d, 2H, J=8 Hz); 6.97-7.01 (m, 1H); 7.07-7.11 (m, 1H); 7.17 (s, 1H); 7.20-7.24 (m, 2H); 7.46-7.54 (m, 4H); 7.86-7.88 (m, 2H); 13.01 (bs, 1H); MS for C36H40N4O5 m/z 609 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe crude residue was purified

Sources & evidence

ORD record
ord-6a2ff5b50bd3420ab6e6265a08c91fe5
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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