Ethyl Acetate → HCID 59563693, compound

HRID 1944128Notes

Reaction equation

HRID 1944128 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:40])[CH:13]([C:23]3[CH:28]=[CH:27][C:26]([O:29][Si](C(C)C)(C(C)C)C(C)C)=[CH:25][CH:24]=3)[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].CCOC(C)=O>C1COCC1>[OH:29][C:26]1[CH:27]=[CH:28][C:23]([CH:13]([C:12]([NH:11][C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[CH:1]=[N:2][CH:3]=[CH:4]3)=[O:40])[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 59563749HCID 59563749, compound

Product 1

HCID 59563693HCID 59563693, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To tert-butyl 3-(isoquinolin-6-ylamino)-3-oxo-2-(4-(triisopropyl silyloxy)phenyl)propylcarbamate (E7) in THF at 0° C. was added TBAF, and the solution was stirred for 45 min at 0° C. The compound was poured into EtOAc and washed with NH4Cl(sat), dried (Na2SO4), filtered, and evaporated. Column chromatography 6% MeOH/CH2Cl2 gave pure tert-butyl 2-(4-hydroxyphenyl)-3-(isoquinolin-6-ylamino)-3-oxopropylcarbamate (E8).

Workup

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

Sources & evidence

ORD record
ord-76491ced768545c68c39c412959cbc41
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

Loading…