Ethyl Acetate → HCID 178454232, compound

HRID 1690232Notes

Reaction equation

HRID 1690232 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.CO[Si](C)(C)C.F[C:20](=[O:35])[C@H:21]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:22]1[CH:26]=[CH:25][S:24][CH:23]=1.CCOC(C)=O>CN(C=O)C>[OH:12][C:8]1[C:9]2[C:4](=[CH:3][C:2]([NH:1][C:20](=[O:35])[C@H:21]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:31])([CH3:33])[CH3:32])[C:22]3[CH:26]=[CH:25][S:24][CH:23]=3)=[CH:11][CH:10]=2)[CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 15771MethoxytrimethylsilaneHCID 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 1

HCID 6228DimethylformamideSolvent

Procedure

To 6-aminoisoquinolin-1-ol in DMF was added methoxytrimethylsilane and (R)-tert-butyl 2-fluoro-2 oxo-1-(thiophen-3-yl)ethylcarbamate and the solution was stirred at room temperature for 6 h. The mixture was poured into EtOAc, washed with NH4Cl (sat)/HCl (1N) followed by 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) (91.8% ee by Chiracel OD-RH).

Workup

  1. washwashed with NH4Cl (sat)/HCl (1N)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-6e28d647e87645e7bf80be4580ec45be
Source dataset
uspto-grants-2012_04
Patent number
US08153654B2

Reaction notes

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