Hydrochloric Acid → HCID 75231082, compound

HRID 2078399Notes

Reaction equation

HRID 2078399 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]([Cl: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]([Cl: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 75231054HCID 75231054, compound

Product 1

HCID 75231082HCID 75231082, compoundYield 102.9%

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-chloro-2-methyl-phenyl) spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (200 mg, 0.33 mmol), LiOH.H2O (280 mg, 6.6 mmol), 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 (200 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-90de5e77d5a340dba115c4db9ca7e830
Source dataset
uspto-grants-2011_04
Patent number
US07928233B2

Reaction notes

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