Hydrochloric Acid → N2-[(2R,3S)-3-Amino-4-(3,5-difluorophenyl)-2-hydroxybutyl]-N1-isobutyl-L-alaninamide dihydrochloride

HRID 14070Notes

Reaction equation

HRID 14070 reaction equation
C(OC(=O)[NH:7][CH:8]([CH2:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[C:25]([F:30])[CH:24]=1)[CH:9]([OH:21])[CH2:10][NH:11][CH:12]([C:14](=[O:20])[NH:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH3:13])(C)(C)C.[ClH:32]>O1CCOCC1>[ClH:32].[ClH:32].[NH2:7][C@@H:8]([CH2:22][C:23]1[CH:24]=[C:25]([F:30])[CH:26]=[C:27]([F:29])[CH:28]=1)[C@H:9]([OH:21])[CH2:10][NH:11][C@H:12]([C:14]([NH:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[O:20])[CH3:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21087184[1-(3,5-Difluoro-benzyl)-2-hydroxy-3-(1-isobutylcarbamoyl-ethylamino)-propyl]-carbamic Acid Tert-Butyl Ester

Product 1

HCID 68607999N2-[(2R,3S)-3-Amino-4-(3,5-difluorophenyl)-2-hydroxybutyl]-N1-isobutyl-L-alaninamide dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

[1-(3,5-Difluoro-benzyl)-2-hydroxy-3-(1-isobutylcarbamoyl-ethylamino)-propyl]-carbamic acid tert-butyl ester (2.7 g, 6 mmol) is dissolved in excess 4N hydrochloric acid in dioxane, and the reaction is stirred 2 h at room temperature. The solution is concentrated under reduced pressure to give the title compound. ESI MS m/z 344.3 [M+H]+.

Workup

  1. concentrationThe solution is concentrated under reduced pressure

Sources & evidence

ORD record
ord-fa99a77f6db142d9a694e0652ad91f8a
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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