2-[3-(2-tert-Butoxycarbonylaminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid ethylester → 2-[3-(2-tert-butoxycarbonylaminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid

HRID 1274399Notes

Reaction equation

HRID 1274399 reaction equation
C([O:3][C:4](=[O:35])[C:5]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=1)=[C:11]2[CH2:25][CH2:26][NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])([CH3:7])[CH3:6])C>[OH-].[Na+]>[C:31]([O:30][C:28]([NH:27][CH2:26][CH2:25][C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[C:8]([C:5]([CH3:7])([CH3:6])[C:4]([OH:35])=[O:3])[CH:9]=2)[NH:13][C:12]=1[C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

3

Reactant 1

HCID 154585222-[3-(2-tert-Butoxycarbonylaminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid ethylester

Product 1

HCID 154585232-[3-(2-tert-butoxycarbonylaminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acidYield 102.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 2-[3-(2-tert-butoxycarbonylaminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methyl-propionic acid ethyl ester (1.28 g in 25 mL ethanol) was added 30 mL of 0.5N sodium hydroxide and the mixture heated to 90° C. on an oil bath. After 30 hours the mixture was concentrated in vacuo, diluted with water and extracted with diethyl ether (3×). The aqueous layer was then made acidic by the addition of 0.5N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo to give the crude title compound (1.23 g).

Workup

  1. concentrationAfter 30 hours the mixture was concentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted with diethyl ether (3×)
  4. additionmade acidic by the addition of 0.5N hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ab345790387406a9957040e092bc658
Source dataset
uspto-grants-2000_12
Patent number
US06156767

Reaction notes

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