Hydrochloric Acid → (S)-methyl 6-(isoquinolin-3-ylcarbamoyloxy)-5-(methylamino)hexanoate

HRID 409770Notes

Reaction equation

HRID 409770 reaction equation
C(O[C:6]([N:8](C)[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][CH3:16])=[O:14])=O)(C)(C)C.Cl>CO>[CH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:30]=[C:21]([NH:20][C:19]([O:18][CH2:17][C@@H:9]([NH:8][CH3:6])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:31])[N:22]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57947397(S)-methyl 5-(tert-butoxycarbonyl(methyl)amino)-6-(isoquinolin-3-ylcarbamoyloxy)hexanoate

Product 1

HCID 57947750(S)-methyl 6-(isoquinolin-3-ylcarbamoyloxy)-5-(methylamino)hexanoateYield 115.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To s solution of (S)-methyl 5-(tert-butoxycarbonyl(methyl)amino)-6-(isoquinolin-3-ylcarbamoyloxy)hexanoate (2.0 g, 4.5 mmol) in MeOH (10 mL) at 0° C. was added HCl (4 M in 1,4-dioxane, 10 mL) dropwise. The solution was stirred at RT for 2 h. The solvents were removed under high vacuum to give (S)-methyl 6-(isoquinolin-3-ylcarbamoyloxy)-5-(methylamino)hexanoate (1.8 g, 94%) as a yellow solid. LRMS (M+H+) m/z 346.2.

Workup

  1. customThe solvents were removed under high vacuum

Sources & evidence

ORD record
ord-52ec29feb3d44123bb37d0584f36190e
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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