Sodium Bicarbonate → HCID 178454232, compound

HRID 539571Notes

Reaction equation

HRID 539571 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([OH:12])=[N:7][CH:6]=[CH:5]2.C([O-])(O)=O.[Na+].F[C:19](=[O:34])[C@H:20]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:21]1[CH:25]=[CH:24][S:23][CH:22]=1>O.C(Cl)Cl>[OH:12][C:8]1[C:9]2[C:4](=[CH:3][C:2]([NH:1][C:19](=[O:34])[C@H:20]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:32])[CH3:31])[C:21]3[CH:25]=[CH:24][S:23][CH:22]=3)=[CH:11][CH:10]=2)[CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 57788121(R)-tert-butyl 2-fluoro-2 oxo-1-(thiophen-3-yl)ethylcarbamateHCID 178507325HCID 178507325, compound

Product 1

HCID 178454232HCID 178454232, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To 6-aminoisoquinolin-1-ol in H2O was added NaHCO3 followed by a solution of (R)-tert-butyl 2-fluoro-2 oxo-1-(thiophen-3-yl)ethylcarbamate in CH2Cl2. The solution was stirred for 4 hours, extracted with EtOAc and NH4Cl(sat)/HCl (1N) and then with NaHCO3 (0.05%), dried (Na2SO4), filtered and evaporated. Column chromatography (SiO2, 5% MeOH, CH2Cl2) gave pure (R)-tert-butyl 2-(1-hydroxyisoquinolin-6-ylamino)-2-oxo-1-(thiophen-3-yl)ethylcarbamate (95% ee by Chiracel OD-RH)

Workup

  1. extractionextracted with EtOAc and NH4Cl(sat)/HCl (1N)
  2. dry with materialwith NaHCO3 (0.05%), dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-6df4d6467bb14a31a51afe15f7f0cb19
Source dataset
uspto-grants-2014_10
Patent number
US08871757B2

Reaction notes

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