Sodium Hydroxide → HCID 58355586, compound

HRID 2168944Notes

Reaction equation

[F:1][C:2]1[C:10]2[N:9]=[C:8]([C:11]([N:13]([CH2:31][CH:32]([CH3:34])[CH3:33])[C@@H:14]3[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17][C@H:16]([C:27]([O:29]C)=[O:28])[CH2:15]3)=[O:12])[N:7]([CH2:35][CH2:36][CH2:37][CH2:38][O:39][CH3:40])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1CO>[C:23]([O:22][C:20]([N:18]1[CH2:19][C@@H:14]([N:13]([C:11]([C:8]2[N:7]([CH2:35][CH2:36][CH2:37][CH2:38][O:39][CH3:40])[C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[C:10]=3[N:9]=2)=[O:12])[CH2:31][CH:32]([CH3:33])[CH3:34])[CH2:15][C@@H:16]([C:27]([OH:29])=[O:28])[CH2:17]1)=[O:21])([CH3:25])([CH3:26])[CH3:24]

Participants

Conditions

Temperature: 45 °C

Procedure

1-tert-Butyl 3-methyl(3R,5S)-5-{{{4-fluoro-1-(4-methoxybutyl)-1H-benzimidazol-2-yl}carbonyl}(2-methylpropyl)amino}piperidine-1,3-dicarboxylate (195 mg) was dissolved in tetrahydrofuran-methanol (1:2, 15 ml), 2M aqueous sodium hydroxide solution (1 ml) was added, and the mixture was stirred at 45° C. for 4 hr. The reaction mixture was concentrated under reduced pressure, neutralized with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, concentration under reduced pressure to give the object product (180 mg).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
extractionextracted with ethyl acetate
dry with materialThe extract was dried over anhydrous magnesium sulfate, concentration under reduced pressure

Sources & evidence

ORD record: ord-963e87f35d494d259e106bc89573c960
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045436B2

Reaction notes

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