Hydrochloric Acid → Isoquinolin-3-yl-carbamic acid (S)-3-benzyloxycarbonylamino-2-methylamino-propyl ester

HRID 409857Notes

Reaction equation

HRID 409857 reaction equation
[CH2:1]([O:8][C:9](=[O:37])[NH:10][CH2:11][C@H:12]([N:28](C(OC(C)(C)C)=O)[CH3:29])[CH2:13][O:14][C:15](=[O:27])[NH:16][C:17]1[N:18]=[CH:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[CH2:1]([O:8][C:9]([NH:10][CH2:11][C@H:12]([NH:28][CH3:29])[CH2:13][O:14][C:15](=[O:27])[NH:16][C:17]1[N:18]=[CH:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:37])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57947594[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-(isoquinolin-3-ylcarbamoyloxy)-propyl]-carbamic acid benzyl ester

Product 1

HCID 57947441Isoquinolin-3-yl-carbamic acid (S)-3-benzyloxycarbonylamino-2-methylamino-propyl esterYield 97.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-(isoquinolin-3-ylcarbamoyloxy)-propyl]-carbamic acid benzyl ester (4.58 g, 9.0 mmol) in MeOH (7.5 mL) was added HCl (4 N in 1,4-dioxane, 22.5 mL, 90.0 mmol). The mixture was stirred at RT for 2 h, concentrated, and re-dissolved in EtOAc. The organic mixture was washed with sat. NaHCO3, water, and brine, dried over Na2SO4, filtered, and concentrated to give Isoquinolin-3-yl-carbamic acid (S)-3-benzyloxycarbonylamino-2-methylamino-propyl ester (3.59 g), which was used without further purification. LRMS (M+H+) m/z 409.2.

Workup

  1. concentrationconcentrated
  2. dissolutionre-dissolved in EtOAc
  3. washThe organic mixture was washed with sat. NaHCO3, water, and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-56108616a2904bcd9358a2898e6cb9b8
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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