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

HRID 1751092Notes

Reaction equation

HRID 1751092 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3([CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][C:21](=[O:28])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:14][CH2:13]3)[C:11](=[O:29])[N:10]([CH2:30][C:31]3[CH:32]=[C:33]([CH:41]=[CH:42][CH:43]=3)[C:34]([O:36]C(C)(C)C)=[O:35])[CH2:9]2)=[CH:4][CH:3]=1>Cl.O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]3([CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][C:21](=[O:28])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:14][CH2:13]3)[C:11](=[O:29])[N:10]([CH2:30][C:31]3[CH:32]=[C:33]([CH:41]=[CH:42][CH:43]=3)[C:34]([OH:36])=[O:35])[CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 58046799Tert-butyl 3-((1-(4-fluorophenyl)-4-oxo-8-(4-oxo-4-phenylbutyl)-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Product 1

HCID 580466523-((1-(4-Fluorophenyl)-4-oxo-8-(4-oxo-4-phenylbutyl)-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acidYield 27.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 3-((1-(4-fluorophenyl)-4-oxo-8-(4-oxo-4-phenylbutyl)-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (100 mg, 0.171 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 to afford the title compound as white powder (25 mg, 23%); 1H NMR (400 MHz, DMSO-d6): δ 1.62 (d, 2H, J=14 Hz); 1.83 (t, 2H, J=6.8 and 7.2 Hz); 2.19-2.28 (m, 2H); 2.44 (t, 2H, J=6.8 Hz); 2.78 (bs, 4H); 3.03 (t, 2H, J=7.2 and 6.8 Hz); 4.54 (s, 2H); 4.59 (s, 2H); 6.81-6.85 (m, 2H); 6.99 (t, 2H, J=8.8 and 9.6 Hz); 7.49-7.53 (m, 4H); 7.62 (t, 1H, J=7.6 Hz); 7.86 (bs, 2H); 7.95-7.97 (m, 2H); 13.1 (bs, 1H); MS for C31H32FN3O4 m/z 530.4 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified

Sources & evidence

ORD record
ord-21d106bd1cea4b159b260bd5a140fe13
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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