Tert-butyl 3-((8-(3-(3-methyl-2-oxoindolin-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate → 3-((8-(3-(3-Methyl-2-oxoindolin-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid

HRID 2363003Notes

Reaction equation

HRID 2363003 reaction equation
[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][CH2:12][CH2:13][N:14]2[CH2:44][CH2:43][C:17]3([N:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:20][N:19]([CH2:28][C:29]4[CH:30]=[C:31]([CH:39]=[CH:40][CH:41]=4)[C:32]([O:34]C(C)(C)C)=[O:33])[C:18]3=[O:42])[CH2:16][CH2:15]2)[C:3]1=[O:45]>Cl.O1CCOCC1>[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][CH2:12][CH2:13][N:14]2[CH2:44][CH2:43][C:17]3([N:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:20][N:19]([CH2:28][C:29]4[CH:30]=[C:31]([CH:39]=[CH:40][CH:41]=4)[C:32]([OH:34])=[O:33])[C:18]3=[O:42])[CH2:16][CH2:15]2)[C:3]1=[O:45]

Participants

4

Reactant 1

HCID 58046750Tert-butyl 3-((8-(3-(3-methyl-2-oxoindolin-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Product 1

HCID 580467433-((8-(3-(3-Methyl-2-oxoindolin-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acidYield 14%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 3-((8-(3-(3-methyl-2-oxoindolin-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (100 mg, 0.164 mmol, 1 equiv) in 4M hydrogen chloride solution in dioxane was stirred at ambient temperature for 16 h. The mixture was concentrated and dried in vacuo to afford the hydrogen chloride salt of the title compound as a white powder (12 mg, 14%); 1H NMR (400 MHz, DMSO-d6): δ 1.34 (d, 3H, J=7.6 Hz); 1.63 (d, 2H, J=12.8 Hz); 1.79 (t, 2H, J=6.8 Hz); 2.49 (bs, 2H); 2.56 (bs, 2H); 2.67-2.77 (m, 4H); 3.45-3.51 (m, 1H); 3.7-3.75 (m, 2H); 4.59 (s, 2H); 4.61 (s, 2H); 6.77 (t, 1H, J=7.2 and 7.6 Hz); 6.86 (d, 2H, J=8.4 Hz); 7.01 (t, 1H, J=7.2 and 7.6 Hz); 7.10 (d, 1H, J=8 Hz); 7.19-7.25 (m, 3H); 7.31 (d, 1H, J=7.2 Hz); 7.48-7.52 (m, 2H); 7.86-7.88 (m, 1H); 13.01 (bs, 1H); MS for C33H36N4O4 m/z 553.11 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customdried in vacuo

Sources & evidence

ORD record
ord-597bc46bc8df4106ad0bd6e9b82ded3b
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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