Sodium Hydroxide → HCID 86651621, compound

HRID 472715Notes

Reaction equation

HRID 472715 reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([C@H:13]([N:15]([CH3:40])[C:16]([N:18]2[CH2:31][CH2:30][C@:21]3([NH:25][CH2:24][CH:23]([C:26]([O:28]C)=[O:27])[CH2:22]3)[CH2:20][C@@H:19]2[C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=2[CH3:39])=[O:17])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-].[Na+:44]>CO.O>[F:42][C:2]([F:1])([F:41])[C:3]1[CH:4]=[C:5]([C@H:13]([N:15]([CH3:40])[C:16]([N:18]2[CH2:31][CH2:30][C@:21]3([NH:25][CH2:24][CH:23]([C:26]([O-:28])=[O:27])[CH2:22]3)[CH2:20][C@@H:19]2[C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=2[CH3:39])=[O:17])[CH3:14])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1.[Na+:44]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58169899HCID 58169899, compound2×

Product 1

HCID 86651621HCID 86651621, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl (5S,7R)-8-{[{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-7-(4-fluoro-2-methylphenyl)-1,8-diazaspiro[4.5]decane-3-carboxylate (Intermediate 36, 22 mg, 0.036 mmol) was dissolved in Methanol (1 ml) and to this solution was added NaOH (1.604 mg, 0.040 mmol) in Water (0.2 ml). The reaction mixture was left stirring at rt overnight. Then the solution was heated at 45° C. for 12 more hrs. The solvents were removed in vacuo and the residue was washed several times with Et2O, the solid was dried under vacuum obtaining the title compound (20.3 mg, 0.033 mmol, 91% yield) as a mixture of diastereoisomers. ratio estimated ca. 2:1, 1H NMR (500 MHz, DMSO-d6) δ ppm 7.99 (s, 1H) 7.70 (s, 2H) 7.04-7.22 (m, 1H) 6.85-6.98 (m, 1H) 6.66-6.82 (m, 1H) 5.20-5.43 (m, 1H) 4.06-4.25 (m, 1H) 2.77 (s, 3H) 2.55-3.57 (m, 5H) 2.33 (s, 3H) 1.46 (d, 3H) 1.06-2.06 (m, 6H);

Workup

  1. waitThe reaction mixture was left
  2. temperatureThen the solution was heated at 45° C. for 12 more hrs
  3. customThe solvents were removed in vacuo
  4. washthe residue was washed several times with Et2O
  5. customthe solid was dried under vacuum

Sources & evidence

ORD record
ord-ab5974a64c444ffb981d25f37e0f53fa
Source dataset
uspto-grants-2014_01
Patent number
US08633214B2

Reaction notes

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