Sodium Hydroxide → HCID 59703554, compound

HRID 556474Notes

Reaction equation

HRID 556474 reaction equation
C[O:2][C:3]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:14][CH3:15])=[CH:10][CH:11]=2)[N:6]1[C:16]1([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)[C:24]2[C:19](=[CH:20][C:21]([Cl:25])=[CH:22][CH:23]=2)[NH:18][C:17]1=[O:26])=[O:4].[OH-].[Na+]>CO.O>[Cl:25][C:21]1[CH:20]=[C:19]2[C:24]([C:16]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=3)([N:6]3[C:7]4[C:12](=[CH:11][CH:10]=[C:9]([O:14][CH3:15])[CH:8]=4)[CH2:13][CH:5]3[C:3]([OH:4])=[O:2])[C:17](=[O:26])[NH:18]2)=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66992271Rac-6'-chloro-3'-(3-chloro-benzyl)-6-methoxy-2'-oxo-2,3,2',3'-tetrahydro-1'h-[1,3']biindolyl-2-carboxylic acid methyl ester

Product 1

HCID 59703554HCID 59703554, compoundYield 103.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of rac-6′-Chloro-3′-(3-chloro-benzyl)-6-methoxy-2′-oxo-2,3,2′,3′-tetrahydro-1′H-[1,3′]biindolyl-2-carboxylic acid methyl ester (250 mg, 0.5 mmol), NaOH (40 mg, 1.0 mmol) in methanol (4 mL) and water (2 mL) was heated to reflux for 3 hr. Then the mixture was concentrated in vacuo to remove methanol. Water (10 mL) was added to the residue. The resulting mixture was acidified with acetic acid, extracted with ethyl acetate. The organic layer was washed with water, dried with Na2SO4, concentrated in vacuo to give 250 mg rac-6′-Chloro-3′-(3-chloro-benzyl)-6-methoxy-2′-oxo-2,3,2′,3′-tetrahydro-1′H-[1,3′]biindolyl-2-carboxylic acid. MS: [M−H]−=481

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hr
  3. concentrationThen the mixture was concentrated in vacuo
  4. customto remove methanol
  5. additionWater (10 mL) was added to the residue
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materialdried with Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c771ae2a6cfa41a89e6c52be26b7ef20
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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