Sodium Hydroxide → HCID 178453553, compound

HRID 632942Notes

Reaction equation

[OH-].[Na+].C[O:4][C:5](=[O:32])[CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:31])[CH2:21][CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1>C1COCC1.CO.O>[C:27]([O:26][C:24]([NH:23][CH2:22][CH2:21][C:20]([NH:19][C:16]1[CH:17]=[CH:18][C:13]([C@H:10]2[CH2:11][CH2:12][C@H:7]([CH2:6][C:5]([OH:32])=[O:4])[CH2:8][CH2:9]2)=[CH:14][CH:15]=1)=[O:31])=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

Conditions

Temperature: 25 °C

Procedure

NaOH (47.8 mg, 1.19 mmol) was added to trans-{4-[4-(3-tert-butoxycarbonylaminopropionylamino)phenyl]cyclohexyl}acetic acid methyl ester (50 mg, 0.12 mmol) dissolved in THF/MeOH/water (20 mL, 3:2:1). The reaction mixture was stirred at 25° C. for 5 hours and concentrated under vacuum. The residue was acidified with 1M HCl up to pH of 2 and extracted with ethyl acetate. The extract was washed with brine and dried with anhydrous sodium sulfate and concentrated under vacuum. Acetonitrile was added thereto and cooled to obtain a filtrate, and the filtrate was filtered and separated to obtain the desired compound (47 mg, 97%) as a white solid.

Workup

concentrationconcentrated under vacuum
extractionextracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried with anhydrous sodium sulfate
concentrationconcentrated under vacuum
additionAcetonitrile was added
temperaturecooled
customto obtain a filtrate
filtrationthe filtrate was filtered
customseparated

Sources & evidence

ORD record: ord-f9b2b8aaafbf4c8a9a29592604546147
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321728B2

Reaction notes

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