Hydrochloric Acid → HCID 76567915, compound

HRID 1728066Notes

Reaction equation

HRID 1728066 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=1[CH:15]1[C:20]2([C:28]3[C:23](=[CH:24][C:25]([Cl:29])=[CH:26][CH:27]=3)[NH:22][C:21]2=[O:30])[CH:19]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=2)[CH2:18][C:17](=[O:38])[NH:16]1)(=O)C.[OH-].[Na+].Cl>O1CCCC1.CO>[Cl:29][C:25]1[CH:24]=[C:23]2[NH:22][C:21](=[O:30])[C:20]3([CH:19]([C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=4)[CH2:18][C:17](=[O:38])[NH:16][CH:15]3[C:9]3[CH:10]=[C:11]([CH3:14])[CH:12]=[CH:13][C:8]=3[O:7][CH2:6][CH2:5][OH:4])[C:28]2=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 76568097HCID 76568097, compound

Product 1

HCID 76567915HCID 76567915, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of racemic (2′R,3R,4′S)-2′-[2-(2-acetoxy-ethoxy)-5-methyl-phenyl]-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.16 g, 0.29 mmol) prepared in example 128c in tetrahydrofuran (30 mL) and methanol (10 mL) was added sodium hydroxide aqueous solution (1N, 10 mL). the reaction mixture was stirred at room temperature for 3 h, then neutralized to “pH” 7 by aqueous HCl. The mixture was then extracted with ethyl acetate. The organic layer was separated, concentrated, and purified by chromatography (EtOAc:MeOH=19:1) to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-[2-(2-hydroxy-ethoxy)-5-methyl-phenyl]spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (70 mg, 47%)

Workup

  1. extractionThe mixture was then extracted with ethyl acetate
  2. customThe organic layer was separated
  3. concentrationconcentrated
  4. custompurified by chromatography (EtOAc:MeOH=19:1)

Sources & evidence

ORD record
ord-623939318e2348c28ed9b4a5af6d6013
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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