Potassium Hydroxide → HCID 15523808, compound

HRID 322222Notes

Reaction equation

HRID 322222 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:38])[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[C@H:27]([CH3:37])[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][C@H:27]([C:13]1[C:12]2[C:16](=[CH:17][CH:18]=[C:10]([C:7]([CH3:9])([CH3:8])[C:6]([OH:38])=[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)[CH3:37])=[O:31])([CH3:34])([CH3:35])[CH3:36]

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 15523807HCID 15523807, compound

Product 1

HCID 15523808HCID 15523808, compoundYield 101.8%

Conditions

Temperature
94 °C

Procedure

To a stirred solution of (S)-2-[3-(2-tert-butoxycarbonylamino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid ethyl ester (2.5 g in 80 mL methanol) was added 26 mL of 2.0N potassium hydroxide and the mixture heated to 94° C. on an oil bath. After 14 hours the mixture was cooled to 0° C., 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 (2.4 g).

Workup

  1. temperatureAfter 14 hours the mixture was cooled to 0° C.
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated ammonium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-20636a747fed42acbe828c5ca4a22967
Source dataset
uspto-grants-2001_04
Patent number
US06211224B1

Reaction notes

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