Ethyl Acetate → HCID 59563703, compound

HRID 1944136Notes

Reaction equation

HRID 1944136 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:41])[CH:13]([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][O:30][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:30][CH2:29][C:26]1[CH:25]=[CH:24][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:41])[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 59563764HCID 59563764, compound

Product 1

HCID 59563703HCID 59563703, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To tert-butyl 3-(isoquinolin-6-ylamino)-3-oxo-2-(4-((triisopropylsilyloxy)methyl)phenyl)propylcarbamate (E138) 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 (MgSO4), filtered, and evaporated. Column chromatography (SiO2, 6% MeOH/CH2Cl2) gave pure tert-butyl 2-(4-(hydroxymethyl)phenyl)-3-(isoquinolin-6-ylamino)-3-oxopropylcarbamate (E139).

Workup

  1. washwashed with NH4Cl(sat)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-151716ef5d884993a8041b35b49ad3f5
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

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