HCID 58046697, compound → HCID 58046800, compound

HRID 1751121Notes

Reaction equation

HRID 1751121 reaction equation
[OH:1][CH:2]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:36][CH2:35][C:9]2([N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][N:11]([CH2:20][C:21]3[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=3)[C:24]([O:26]C(C)(C)C)=[O:25])[C:10]2=[O:34])[CH2:8][CH2:7]1>Cl.O1CCOCC1>[OH:1][CH:2]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([N:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:12][N:11]([CH2:20][C:21]3[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=3)[C:24]([OH:26])=[O:25])[C:10]2=[O:34])[CH2:35][CH2:36]1

Participants

4

Reactant 1

HCID 58046697HCID 58046697, compound

Product 1

HCID 58046800HCID 58046800, compoundYield 44.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution tert-butyl 3-((8-(4-hydroxy-4-phenylbutyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (300 mg, 0.527 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 high performance liquid chromatography to afford the acetate salt of the title compound as a white solid (120 mg, 44.4%); 1H NMR (400 MHz, DMSO-d6): δ 1.38-1.52 (m, 2H); 1.60 (d, 2H, J=13.2 Hz); 1.84-1.94 (m, 2H); 2.41 (t, 2H, J=7.2 and 7.6 Hz); 2.53-2.59 (m, 2H); 2.69-2.75 (m, 4H); 4.58 (s, 2H); 4.61 (s, 2H); 5.84 (t, 1H, J=6.8 and 6.4 Hz); 6.74 (t, 1H, J=7.6 and 7.2 Hz); 6.81 (s, 1H); 6.83 (s, 1H); 7.16-7.20 (m, 2H); 7.31-7.38 (m, 5H); 7.48-754 (m, 2H); 7.86-7.88 (m, 2H); 8.30 (S, 1H); 12.8 (bs, 1H); MS for C31H35N3O4 m/z 514.4 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified

Sources & evidence

ORD record
ord-7c1ad0dc693a44669383d91f34d1948b
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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