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 1532383Notes

Reaction equation

HRID 1532383 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-046db8e5eb76475c8f76e1734c5471a7
Source dataset
uspto-grants-2001_03
Patent number
US06200957B1

Reaction notes

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