Potassium Hydroxide → HCID 21886799, compound

HRID 722929Notes

Reaction equation

HRID 722929 reaction equation
[OH-].[K+].C([N:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15](=[O:38])[CH2:16][CH2:17][CH2:18][CH2:19][N:20]([CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH3:37])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:12][CH:13]=2)[CH2:8][CH2:7]1)(=O)C>CO>[NH:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15](=[O:38])[CH2:16][CH2:17][CH2:18][CH2:19][N:20]([CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH3:37])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:12][CH:13]=2)[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 21887260HCID 21887260, compound

Product 1

HCID 21886799HCID 21886799, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of potassium hydroxide (0.22 g) in methanol (4 ml) was added at room temperature to tert-butyl 5-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-5-oxopentyl[2-(2-methoxyphenyl)ethyl]carbamate (1.00 g) obtained in Reference Example 47, and heated at reflux for 2 hours with stirring. The solvent was evaporated under reduced pressure, water was added to the resulting residue, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluting solvent; hexane: ethyl acetate=1:1) to give the title compound as a pale yellow oil (700 mg).

Workup

  1. customobtained in Reference Example 47
  2. temperatureheated
  3. temperatureat reflux for 2 hours
  4. customThe solvent was evaporated under reduced pressure, water
  5. additionwas added to the resulting residue
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe resulting residue was purified by silica gel chromatography (eluting solvent; hexane: ethyl acetate=1:1)

Sources & evidence

ORD record
ord-d65b5f61865c4dc89f13b2bbeb0d69e8
Source dataset
uspto-grants-2006_11
Patent number
US07138533B2

Reaction notes

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