Sodium Hydroxide → HCID 58355316, compound

HRID 1509606Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[N:10]=[N:9][C:8]=1[C:19]([N:21]([CH2:39][CH:40]([CH3:42])[CH3:41])[C@@H:22]1[CH2:27][N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:25][C@H:24]([C:35]([O:37]C)=[O:36])[CH2:23]1)=[O:20].[OH-].[Na+]>CO>[C:31]([O:30][C:28]([N:26]1[CH2:27][C@@H:22]([N:21]([C:19]([C:8]2[N:9]=[N:10][N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[C:7]=2[CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[O:20])[CH2:39][CH:40]([CH3:41])[CH3:42])[CH2:23][C@@H:24]([C:35]([OH:37])=[O:36])[CH2:25]1)=[O:29])([CH3:32])([CH3:34])[CH3:33]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 1-tert-butyl 3-methyl (3R,5S)-5-[{[5-(4-methoxybutyl)-1-(2-methylphenyl)-1H-1,2,3-triazol-4-yl]carbonyl}(2-methylpropyl)amino]piperidine-1,3-dicarboxylate (1.47 g) in methanol (10 ml) was added 4N aqueous sodium hydroxide solution (5 ml), and the mixture was stirred at 50° C. for 30 min. The solvent was concentrated under reduced pressure, and the residue was neutralized with 10% aqueous citric acid solution, extracted with ethyl acetate (30 ml×2) and the extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the object product (1.3 g) as an amorphous compound.

Workup

concentrationThe solvent was concentrated under reduced pressure
extractionextracted with ethyl acetate (30 ml×2)
dry with materialthe extract was dried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-81ef43524dce4cbf8662b9a5eeb6fe3f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221836B2

Reaction notes

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