Sodium Hydroxide → HCID 58355586, compound

HRID 1509459Notes

Reaction equation

HRID 1509459 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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58355473HCID 58355473, compound

Product 1

HCID 58355586HCID 58355586, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

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

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

Sources & evidence

ORD record
ord-7743b14fcfc24707a441d288d57fd0d6
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

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