Hydrochloric Acid → (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-isopropylbenzyl)amino]butan-2-ol Dihydrochloride

HRID 348876Notes

Reaction equation

HRID 348876 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([F:32])[CH:31]=1)[CH2:5][C@H:6]([NH:21]C(=O)OC(C)(C)C)[C@H:7]([OH:20])[CH2:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([CH3:19])[CH3:18])[CH:12]=1.[ClH:33]>O1CCOCC1>[ClH:33].[ClH:33].[NH2:21][C@@H:6]([CH2:5][C:4]1[CH:29]=[C:30]([F:32])[CH:31]=[C:2]([F:1])[CH:3]=1)[C@H:7]([OH:20])[CH2:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([CH3:19])[CH3:18])[CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58802705HCID 58802705, compound

Product 1

HCID 57487288(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-isopropylbenzyl)amino]butan-2-ol Dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl (1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(3-isopropylbenzyl)amino]propylcarbamate (1.5 g, 3.3 mmol) is dissolved in 4 N hydrochloric acid in dioxane (20 mL), and the reaction is stirred at room temperature 3 h. The mixture is concentrated under reduced pressure to afford the title compound. ESI MS m/z 349.2 [M+H]+.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-39c6301b2f874c71988bdfcc19382c2c
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

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