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

HRID 1509503Notes

Reaction equation

[CH3:1][CH:2]([CH3:41])[CH2:3][N:4]([C:22]([C:24]1[N:28]([CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:27]2[CH:37]=[CH:38][CH:39]=[CH:40][C:26]=2[N:25]=1)=[O:23])[C@@H:5]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][C@H:7]([C:18]([O:20]C)=[O:19])[CH2:6]1.[OH-].[Na+].Cl>CO>[C:14]([O:13][C:11]([N:9]1[CH2:10][C@@H:5]([N:4]([CH2:3][CH:2]([CH3:1])[CH3:41])[C:22]([C:24]2[N:28]([CH2:29][CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:27]3[CH:37]=[CH:38][CH:39]=[CH:40][C:26]=3[N:25]=2)=[O:23])[CH2:6][C@@H:7]([C:18]([OH:20])=[O:19])[CH2:8]1)=[O:12])([CH3:15])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 50 °C

Procedure

1-tert-Butyl 3-methyl (3R,5S)-5-[(2-methylpropyl){[1-(2-phenylethyl)-1H-benzimidazol-2-yl]carbonyl}amino]piperidine-1,3-dicarboxylate (1.12 g) was dissolved in methanol, 2M aqueous sodium hydroxide solution (10 ml) was added dropwise at room temperature. The reaction mixture was stirred at 50° C. for 3 hr. The reaction mixture was 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 to give the object product (1.07 g).

Workup

extractionextracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-8b0289974ee84aaa9826e9d1bfb53c32
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221836B2

Reaction notes

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