Hydrochloric Acid → HCID 75231052, compound

HRID 2078398Notes

Reaction equation

HRID 2078398 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:40])[C:10]3([CH:15]([C:16]4[C:17]([O:23][C:24]([C:27]([O:29]C)=[O:28])([CH3:26])[CH3:25])=[N:18][CH:19]=[C:20]([Cl:22])[CH:21]=4)[CH2:14][C:13](=[O:31])[NH:12][CH:11]3[C:32]3[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=3[CH3:39])[C:5]2=[CH:4][CH:3]=1.O[Li].O.O.Cl>CO>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:40])[C:10]3([CH:15]([C:16]4[C:17]([O:23][C:24]([C:27]([OH:29])=[O:28])([CH3:25])[CH3:26])=[N:18][CH:19]=[C:20]([Cl:22])[CH:21]=4)[CH2:14][C:13](=[O:31])[NH:12][CH:11]3[C:32]3[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=3[CH3:39])[C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 75231051HCID 75231051, compound

Product 1

HCID 75231052HCID 75231052, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of racemic (2′S, 3S, 4′R)-6-chloro-4′-[5-chloro-2-(1-methoxycarbonyl-1-methyl-ethoxy)-pyridin-3-yl]-2′-(5-fluoro-2-methyl-phenyl) spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (160 mg, 0.27 mmol), LiOH.H2O (250 mg, 5.94 mol), H2O (5 mL) and methanol (15 mL) was heated at 80° C. for 40 min. After cooled to room temperature, the solution was acidified to “pH” 1 by addition of 1N HCl solution. The aqueous layer was extracted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous Na2SO4 and concentrated to give the title compound as a light yellow solid (140 mg).

Workup

  1. temperatureAfter cooled to room temperature
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c80590c4f6954420915274a5cbec8920
Source dataset
uspto-grants-2011_04
Patent number
US07928233B2

Reaction notes

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