Potassium Hydroxide → HCID 15523808, compound

HRID 1275180Notes

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

Reactant 2

HCID 14797Potassium Hydroxide

HCID 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

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

Sources & evidence

ORD record: ord-d0552f93509249d186dd2b142799890f
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06159989

Reaction notes

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