Hydrochloric Acid → (3R,5S)-(tert-butoxycarbonyl)-5-[{[6-fluoro-1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-3-carboxylic acid

HRID 1184092Notes

Reaction equation

HRID 1184092 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10]([N:12]([CH2:30][CH:31]([CH3:33])[CH3:32])[C@@H:13]3[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16][C@H:15]([C:26]([O:28]C)=[O:27])[CH2:14]3)=[O:11])[N:7]([CH2:34][CH2:35][CH2:36][CH2:37][O:38][CH3:39])[C:6]=2[CH:40]=1.[OH-].[Na+].Cl>C(O)C>[C:22]([O:21][C:19]([N:17]1[CH2:18][C@@H:13]([N:12]([C:10]([C:8]2[N:7]([CH2:34][CH2:35][CH2:36][CH2:37][O:38][CH3:39])[C:6]3[CH:40]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[N:9]=2)=[O:11])[CH2:30][CH:31]([CH3:32])[CH3:33])[CH2:14][C@@H:15]([C:26]([OH:28])=[O:27])[CH2:16]1)=[O:20])([CH3:24])([CH3:25])[CH3:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58355630HCID 58355630, compound

Product 1

HCID 58355153(3R,5S)-(tert-butoxycarbonyl)-5-[{[6-fluoro-1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-3-carboxylic acidYield 99.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

1-tert-Butyl 3-methyl (3R,5S)-5-[{[6-fluoro-1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-1,3-dicarboxylate (1.6 g) was dissolved in ethanol (100 ml), 2M aqueous sodium hydroxide solution (14.2 ml) was added, and the mixture was stirred at 50° C. for 5 hr. The reaction mixture was cooled to room temperature, adjusted to pH 7 with 1M hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate was concentrated under reduced pressure to give the object product (1.55 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washa fraction eluted with ethyl acetate
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-08d32d1c41724ee5ba680cfc990bdd2a
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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