Tetrabutylammonium Fluoride → HCID 59563761, compound

HRID 1944171Notes

Reaction equation

HRID 1944171 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:41])[CH:13]([C:24]3[CH:29]=[CH:28][C:27]([O:30][Si](C(C)C)(C(C)C)C(C)C)=[CH:26][CH:25]=3)[CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:30][C:27]1[CH:28]=[CH:29][C:24]([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][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59563770HCID 59563770, compound

Product 1

HCID 59563761HCID 59563761, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To tert-butyl 4-(isoquinolin-6-ylamino)-4-oxo-3-(4-(triisopropylsilyloxy)phenyl)butylcarbamate (E306) in THF at 0° C. was added TBAF and the solution was stirred at 0° C. for 30 min. The solution was poured into NH4Cl(sat) and extracted with EtOAc. The combined organics were dried (Na2SO4), filtered, and evaporated. Column chromatography (SiO2, 5-8% MeOH/CH2Cl2) gave pure tert-butyl 3-(4-hydroxyphenyl)-4-(isoquinolin-6-ylamino)-4-oxobutylcarbamate (E307).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organics were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-bcb59bce6fd44c39b858f83fea250b20
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

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