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

HRID 1274385Notes

Reaction equation

HRID 1274385 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:37])[C:7]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[CH:20]=1)=[C:13]2[CH2:27][CH2:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])([CH3:9])[CH3:8])C>>[C:33]([O:32][C:30]([NH:29][CH2:28][CH2:27][C:13]1[C:12]2[C:16](=[CH:17][CH:18]=[C:10]([C:7]([CH3:9])([CH3:8])[C:6]([OH:37])=[O:5])[CH:11]=2)[NH:15][C:14]=1[C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[CH:20]=1)=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 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 99%

Conditions

Temperature
94 °C

Procedure

To a stirred solution of 2-[3-(2-tert-butoxycarbonylaminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid ethyl ester (665 mg in 20 mL methanol) was added 7 mL of 2.0N potassium hydroxide and the mixture heated to 94° C. on an oil bath. After 6 hours the mixture was acidified to pH5 and extracted with ethyl acetate. The organic layer was washed with saturated ammonium chloride, dried over sodium sulfate and concentrated in vacuo to give the crude title compound (620 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated ammonium chloride
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03b8d0f39241464a89a2f4b7dd4fe7bd
Source dataset
uspto-grants-2000_12
Patent number
US06156767

Reaction notes

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