Lithium Hydroxide → HCID 67812545, compound

HRID 1290025Notes

Reaction equation

HRID 1290025 reaction equation
C[O:2][C:3](=[O:37])[C@H:4]([CH3:36])[NH:5][C:6](=[O:35])[CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]2[C:19](=[O:34])[NH:20][C:21](=[O:33])[C:22]=2[C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([CH3:32])[CH:24]=2)=[CH:10]1.[OH-].[Li+]>O1CCOCC1.O>[CH3:32][N:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23]([C:22]2[C:21](=[O:33])[NH:20][C:19](=[O:34])[C:18]=2[C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]([CH2:8][CH2:7][C:6]([NH:5][C@H:4]([C:3]([OH:37])=[O:2])[CH3:36])=[O:35])[CH:10]=2)=[CH:24]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67811148HCID 67811148, compound

Product 1

HCID 67812545HCID 67812545, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

3-[3-[4-(1-Methylindol-3-yl)-1H-pyrrole-2,5-dion-3-yl)-indol-1-yl]-propionyl-L-alanine methyl ester 100 mg (0.2 mmol) are dissolved in a mixture of 4 mL dioxane and 1 mL of water, mixed with 36 mg (1.5 mmol) lithium hydroxide, and stirred for 18 hours at ambient temperature. The solvent is subsequently distilled off in a vacuum and the residue is taken up in 30 mL ethylacetate, washed with 1N hydrochloric acid, and dried over anhydrous sodium sulphate. The solvent is then distilled off in a vacuum and the residue separated by thick layer chromatography (silica gel, dichloromethane/methanol saturated with ammonia=90:10%). The product is separated with the first polar fraction, extracted, freed from solvent, and stirred up with a mixture of dichloromethane and diisopropyl ether (1:1). There are obtained 65 mg (67% of theory) of the desired product;

Workup

  1. distillationThe solvent is subsequently distilled off in a vacuum
  2. washwashed with 1N hydrochloric acid
  3. dry with materialdried over anhydrous sodium sulphate
  4. distillationThe solvent is then distilled off in a vacuum
  5. customthe residue separated by thick layer chromatography (silica gel, dichloromethane/methanol saturated with ammonia=90:10%)
  6. customThe product is separated with the first polar fraction
  7. extractionextracted
  8. stirringstirred up with a mixture of dichloromethane and diisopropyl ether (1:1)

Sources & evidence

ORD record
ord-2047fc9e15fb4deb93dcd8bd7cb9c871
Source dataset
uspto-grants-1998_05
Patent number
US05750555

Reaction notes

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