Tert-butyl 2-(4-oxo-8-(4-oxo-4-phenylbutyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)benzoate → 2-(4-Oxo-8-(4-oxo-4-phenylbutyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)benzoic acid

HRID 2363057Notes

Reaction equation

HRID 2363057 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][C:15](=[O:22])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:8][CH2:7]2)[N:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:4][N:3]1[C:29]1[CH:41]=[CH:40][CH:39]=[CH:38][C:30]=1[C:31]([O:33]C(C)(C)C)=[O:32]>Cl.O1CCOCC1>[O:1]=[C:2]1[C:6]2([CH2:7][CH2:8][N:9]([CH2:12][CH2:13][CH2:14][C:15](=[O:22])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:11]2)[N:5]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:4][N:3]1[C:29]1[CH:41]=[CH:40][CH:39]=[CH:38][C:30]=1[C:31]([OH:33])=[O:32]

Participants

4

Reactant 1

HCID 58046637Tert-butyl 2-(4-oxo-8-(4-oxo-4-phenylbutyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)benzoate

Product 1

HCID 580467242-(4-Oxo-8-(4-oxo-4-phenylbutyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)benzoic acidYield 43.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 2-(4-oxo-8-(4-oxo-4-phenylbutyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)benzoate (410 mg, 0.741 mmol, 1 equiv) in 4M hydrogen chloride solution in dioxane was stirred at ambient temperature for 5 h. The mixture was concentrated in vacuo and purified using preparative thin layer chromatography in 10% methanol in dichloromethane. The isolated mixture was treated with 4M hydrogen chloride solution in dioxane to afford the hydrogen chloride salt of the title compound as a white powder (160 mg, 43.5%); 1H NMR (400 MHz, DMSO-d6): δ 2.05-2.08 (m, 4H); 3.04 (m, 2H); 3.16 (m, 2H); 3.22 (t, 2H, J=6.8 and 7.4 Hz); 3.56-3.71 (m, 4H); 5.10 (s, 2H); 6.84 (t, 1H, J=7.2 Hz); 7.14 (s, 1H); 7.16 (s, 1H); 7.25-7.29 (m, 2H); 7.52-7.57 (m, 3H); 7.63-7.68 (m, 2H); 7.71-7.75 (m, 1H); 7.94 (dd, 1H, J=1.2 Hz); 7.98-8.00 (m, 2H); 10.61 (bs, 1H); 13.22 (bs, 1H); MS for C30H31N3O4 m/z 498.3 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified
  3. additionThe isolated mixture was treated with 4M hydrogen chloride solution in dioxane

Sources & evidence

ORD record
ord-6f5feb3728814709be9f4b713e6e000f
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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