Tetrabutylammonium Fluoride → 2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-hydroxypropyl)phenyl)-N-(3-nitrobenzyl)acetamide

HRID 735705Notes

Reaction equation

HRID 735705 reaction equation
[C:1]([O:5][C:6]([N:8]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[C:9]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][CH:20]([C:34]3[CH:39]=[CH:38][C:37]([CH2:40][CH:41]([O:43][Si](C(C)(C)C)(C)C)[CH3:42])=[CH:36][CH:35]=3)[C:21]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[CH:26]=3)=[O:22])=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:54]([O:53][C:51]([N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[C:9]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][CH:20]([C:34]3[CH:35]=[CH:36][C:37]([CH2:40][CH:41]([OH:43])[CH3:42])=[CH:38][CH:39]=3)[C:21]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[CH:26]=3)=[O:22])=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1)=[O:52])([CH3:57])([CH3:55])[CH3:56]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 578426342-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-(tert-butyldimethylsilyloxy)propyl)phenyl)-N-(3-nitrobenzyl)acetamide

Product 1

HCID 578427332-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)-2-(4-(2-hydroxypropyl)phenyl)-N-(3-nitrobenzyl)acetamideYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of 77E (172 mg, 0.215 mmol) in 3 mL THF, was added a solution of TBAF (1M in THF, 1 mL, 1 mmol). The mixture was stirred at 35° C. for 17 h, then concentrated. The residue was dissolved in EtOAc, washed with water (2×) and brine, dried (Na2SO4) and concentrated. Purification by flash chromatography (0 to 100% EtOAc/hexanes) afforded 38 mg (26%) of 77F as a yellow glass. MS (ESI) m/z 686.4 (M+H)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with water (2×) and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification by flash chromatography (0 to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0ceb246662064ed5b313039a700e59ab
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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