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

HRID 1751082Notes

Reaction equation

HRID 1751082 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[CH2:29][C:30]1[CH:42]=[CH:41][CH:40]=[CH:39][C:31]=1[C:32]([O:34]C(C)(C)C)=[O:33]>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[CH2:29][C:30]1[CH:42]=[CH:41][CH:40]=[CH:39][C:31]=1[C:32]([OH:34])=[O:33]

Participants

4

Reactant 1

HCID 58046688Tert-butyl 2-((4-oxo-8-(4-oxo-4-phenylbutyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Product 1

HCID 547719852-((4-Oxo-8-(4-oxo-4-phenylbutyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acidYield 33.1%

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)methyl)benzoate (268 mg, 0.472 mmol, 1 equiv) in 4M hydrogen chloride solution in dioxane was stirred at ambient temperature for 4 h. The mixture was concentrated in vacuo and purified using preparative thin layer chromatography in 7% methanol in dichloromethane. The pure extract was treated with 4M hydrogen chloride solution in dioxane to afford the hydrogen chloride salt of the title compound as a white powder (80 mg, 30%); 1H NMR (400 MHz, DMSO-d6): δ 2.01 (d, 2H, J=14.4 Hz); 2.09 (t, 2H, J=7.2 and 7.6 Hz); 3.02 (t, 2H, J=12.4 and 10.4 Hz); 3.18 (bs, 2H); 3.23 (t, 2H, J=7.2 and 6.8 Hz); 3.65-3.7 (m, 4H); 4.69 (s, 2H); 4.94 (s, 2H); 6.81 (t, 1H, J=7.2 and 7.6 Hz); 7.04 (d, 2H, J=8.4 Hz); 7.24 (t, 2H, J=7.6 and 8 Hz); 7.33 (d, 1H, J=8 Hz); 7.43 (t, 2H, J=7.6 Hz); 7.53-7.61 (m, 3H); 7.66 (t, 1H, J=7.6 Hz); 7.93 (dd, 1H, J=1.2 and 1.6 Hz); 7.99-8.01 (m, 2H); 10.5 (bs, 1H); 13.2 (bs, 1H); MS for C31H33N3O4 m/z 512.4 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified
  3. extractionThe pure extract
  4. additionwas treated with 4M hydrogen chloride solution in dioxane

Sources & evidence

ORD record
ord-439ffefb64aa4e93b1f1b6d052489eab
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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