Hydrochloric Acid → HCID 57947387, compound

HRID 340910Notes

Reaction equation

HRID 340910 reaction equation
[F:1][C:2]1[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:3]=1[CH2:4][NH:5][C:6](=[O:32])[N:7]([C@H:9]([CH2:17][O:18][C:19](=[O:31])[NH:20][C:21]1[N:22]=[CH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:10][CH2:11][CH2:12][C:13]([O:15]C)=[O:14])[CH3:8].[Li+].[OH-].Cl>O1CCOCC1>[F:1][C:2]1[C:36]([F:37])=[CH:35][CH:34]=[CH:33][C:3]=1[CH2:4][NH:5][C:6](=[O:32])[N:7]([C@H:9]([CH2:17][O:18][C:19](=[O:31])[NH:20][C:21]1[N:22]=[CH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57947656HCID 57947656, compound

Product 1

HCID 57947387HCID 57947387, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-methyl 5-(3-(2,3-difluorobenzyl)-1-methylureido)-6-(isoquinolin-3-ylcarbamoyloxy)hexanoate (1.45 g, 2.04 mmol, 1.0 equiv.) in 1,4-dioxane (18 mL) was added aqueous LiOH (6.12 mL, 6.12 mmol, 3.0 equiv.) at RT After stirred at RT for 1 h, the reaction mixture was acidified with HCl (1.0 N) to pH ˜3. The mixture was extracted with EtOAc twice. The combined EtOAc solution was washed with brine, dried over Na2SO4, and concentrated under vacuum to give (S)-5-(3-(2,3-difluorobenzyl)-1-methylureido)-6-(isoquinolin-3-ylcarbamoyloxy)hexanoic acid, which was used without further purification. LRMS (M+H+) m/z 501.3.

Workup

  1. extractionThe mixture was extracted with EtOAc twice
  2. washThe combined EtOAc solution was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ca9003c525184cea843d79b03ab1e471
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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