Sodium Hydroxide → HCID 58355160, compound

HRID 2169081Notes

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][CH:13]=2)[N:10]=[N:9][C:8]=1[C:18]([N:20]([CH2:38][CH:39]([CH3:41])[CH3:40])[C@@H:21]1[CH2:26][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:24][C@H:23]([C:34]([O:36]C)=[O:35])[CH2:22]1)=[O:19].[OH-].[Na+]>CO>[C:30]([O:29][C:27]([N:25]1[CH2:26][C@@H:21]([N:20]([C:18]([C:8]2[N:9]=[N:10][N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:7]=2[CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[O:19])[CH2:38][CH:39]([CH3:40])[CH3:41])[CH2:22][C@@H:23]([C:34]([OH:36])=[O:35])[CH2:24]1)=[O:28])([CH3:32])([CH3:33])[CH3:31]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 1-tert-butyl 3-methyl(3R,5S)-5-[{[5-(4-methoxybutyl)-1-phenyl-1H-1,2,3-triazol-4-yl]carbonyl}(2-methylpropyl)amino]piperidine-1,3-dicarboxylate (1.715 g) in methanol (10 ml) was added 4N aqueous sodium hydroxide solution (10 ml), and the mixture was stirred at 65° C. for 30 min. The solvent was concentrated under reduced pressure, and the residue was neutralized with 10% aqueous citric acid solution. The mixture was extracted with ethyl acetate (20 ml×2) and the extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the object product (1.56 g) as an amorphous compound.

Workup

concentrationThe solvent was concentrated under reduced pressure
extractionThe mixture was extracted with ethyl acetate (20 ml×2)
dry with materialthe extract was dried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-860744bd144c4f7b852a5339cb18bf83
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045436B2

Reaction notes

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