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Hydrochloric Acid → 3-((1-Cyclohexyl-8-(4-(4-fluorophenyl)-4-oxobutyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid, hydrochloride

HRID 2363008
Notes
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Reaction equation

HRID 2363008 reaction equation
[CH:1]1([N:7]2[C:11]3([CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][C:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)=[O:21])[CH2:13][CH2:12]3)[C:10](=[O:29])[N:9]([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])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:44]>O1CCOCC1>[ClH:44].[CH:1]1([N:7]2[C:11]3([CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][C:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)=[O:21])[CH2:13][CH2:12]3)[C:10](=[O:29])[N:9]([CH2:30][C:31]3[CH:32]=[C:33]([CH:41]=[CH:42][CH:43]=3)[C:34]([OH:36])=[O:35])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58046778Tert-butyl 3-((1-cyclohexyl-8-(4-(4-fluorophenyl)-4-oxobutyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Product 1

HCID 1317312993-((1-Cyclohexyl-8-(4-(4-fluorophenyl)-4-oxobutyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid, hydrochlorideYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-butyl 3-((1-cyclohexyl-8-(4-(4-fluorophenyl)-4-oxobutyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.39 g, 0.659 mmol) and 4M hydrochloric acid/1% triethylsilane in 1,4-dioxane (6 mL) were stirred at room temperature for 4 hours. The reaction was evaporated and the residue purified by PTLC (10% methanol/dichloromethane). The product obtained from PTLC was redissolved in 4M hydrochloric acid in dioxane and evaporated. The residue was dissolved in acetonitrile (5 mL) and water (5 mL) and lyophilized to give product as a white solid (0.28 g, 75%); HPLC rt 10.92 min; NMR (DMSO-d6); δ1.02-1.08 (m, 1H); 1.18-1.28 (m, 4H); 1.28-1.40 (m, 1H); 1.45-1.65 (m, 2H); 1.65-1.78 (m, 3H); 1.85-2.10 (m, 3H); 2.33-2.50 (m, 2H); 3.10 (m, 2H); 3.22 (t, J=6.8 Hz, 2H); 3.49-3.56 (m, 5H); 4.52 (s, 2H); 7.35-7.40 (m, 2H); 7.50 (m, 2H); 7.85-7.86 (m, 2H); 8.05-8.09 (m, 2H); 10.6 (br s, 1H); 13.0 (br s, 1H); MS for C31H38FN3O4 m/z 536 (M+H)+.

Workup

  1. customThe reaction was evaporated
  2. customthe residue purified by PTLC (10% methanol/dichloromethane)
  3. dissolutionwas redissolved in 4M hydrochloric acid in dioxane
  4. customevaporated
  5. dissolutionThe residue was dissolved in acetonitrile (5 mL)

Sources & evidence

ORD record
ord-ed528971f0f349d28ef5c934df23d0dd
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08691836B2

Reaction notes

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