Hydrochloric Acid → N-[(1S,2R)-1-benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]amino}propyl]-1-oxo-2-(1-propylbutyl)isoindoline-4-carboxamide hydrochloride

HRID 387618Notes

Reaction equation

HRID 387618 reaction equation
[CH2:1]([C@H:8]([NH:24][C:25]([C:27]1[C:28]2[CH2:29][N:30]([CH:37]([CH2:41][CH2:42][CH3:43])[CH2:38][CH2:39][CH3:40])[C:31](=[O:36])[C:32]=2[CH:33]=[CH:34][CH:35]=1)=[O:26])[C@H:9]([OH:23])[CH2:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:44]>CCOCC.O1CCOCC1>[ClH:44].[CH2:1]([C@H:8]([NH:24][C:25]([C:27]1[C:28]2[CH2:29][N:30]([CH:37]([CH2:41][CH2:42][CH3:43])[CH2:38][CH2:39][CH3:40])[C:31](=[O:36])[C:32]=2[CH:33]=[CH:34][CH:35]=1)=[O:26])[C@H:9]([OH:23])[CH2:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:21])([F:22])[F:20])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 25206129N-[(1S,2R)-1-Benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]amino}propyl]-1-oxo-2-(1-propylbutyl)isoindoline-4-carboxamide

Product 1

HCID 25206128N-[(1S,2R)-1-benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]amino}propyl]-1-oxo-2-(1-propylbutyl)isoindoline-4-carboxamide hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

110 mg of N-[(1S,2R)-1-benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]amino}propyl]-1-oxo-2-(1-propylbutyl)isoindoline-4-carboxamide are dissolved in 8 cm3 of ether at a temperature close to 20° C. 0.5 cm3 of a 4M solution of hydrochloric acid in dioxane is added while stirring under argon. The reaction mixture precipitates. The precipitate is filtered under a slight vacuum, washed with 2 lots of 5 cm3 of ethyl ether then dried in a dessicator for 2 h. 80 mg of N-[(1S,2R)-1-benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]amino}propyl]-1-oxo-2-(1-propylbutyl)isoindoline-4-carboxamide hydrochloride (1:1) is obtained in the form of a white solid.

Workup

  1. customclose to 20° C
  2. customThe reaction mixture precipitates
  3. filtrationThe precipitate is filtered under a slight vacuum
  4. washwashed with 2 lots of 5 cm3 of ethyl ether
  5. customthen dried in a dessicator for 2 h

Sources & evidence

ORD record
ord-eccd277744bc49b4bc8a6f3c369a3de3
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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