Hydrochloric Acid → HCID 58046751, compound

HRID 1751067Notes

Reaction equation

HRID 1751067 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:31]=[C:32]([CH:40]=[CH:41][CH:42]=1)[C:33]([O:35]C(C)(C)C)=[O:34].Cl>O1CCOCC1.C([SiH](CC)CC)C>[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:17]=[CH:18][CH:19]=[CH:20][CH:21]=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:31]=[C:32]([CH:40]=[CH:41][CH:42]=1)[C:33]([OH:35])=[O:34]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58046804HCID 58046804, compound

Product 1

HCID 58046751HCID 58046751, compound

Reagents, catalysts & solvents 2

HCID 12052TriethylsilaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl 3-((4-oxo-8-(4-oxo-4-phenylbutyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.1 g, 0.18 mmol) was added 4M solution of HCl in dioxane (2 mL) and triethylsilane (0.1 mL). After stirring at room temperature for 4 hours, the reaction mixture was concentrated in vacuo and isolated by reverse phase HPLC to obtain the title compound as an acetate salt (0.044 g, 43%); 1H NMR (DMSO-d6): δ 1.58 (d, 2H, J=13.6 Hz), 1.84 (t, 2H, J=6.8 Hz), 2.42-2.53 (m, 4H), 2.74-2.78 (m, 4H), 3.05 (t, 2H, J=7.2 Hz), 4.58 (d, 4H, J=13.2 Hz), 6.70-6.75 (m, 3H), 7.12 (t, 2H, J=7.2 Hz), 7.48-7.54 (m, 3H), 7.63 (t, 2H, J=7.6 Hz), 7.85 (d, 2H, J=2 Hz), 7.98 (dd, 2H, J=8 and 1.6 Hz); MS for C31H33N3O4 m/z 512.07 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customisolated by reverse phase HPLC

Sources & evidence

ORD record
ord-0e2dd3ad9fe84082adf503ccc3c3b491
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

Loading…