Water → HCID 44419226, compound

HRID 1364574Notes

Reaction equation

HRID 1364574 reaction equation
[CH3:1][S:2]([C:5]1[CH:36]=[CH:35][C:8]([CH2:9][NH:10][C:11]([C:13]2[CH:18]=[C:17]([NH2:19])[C:16]([C:20]([Si](C)(C)C)=[CH:21][C:22]#[C:23][Si](C)(C)C)=[C:15]([O:32][CH2:33][CH3:34])[N:14]=2)=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>O1CCCC1>[NH2:19][C:17]1[C:16](/[CH:20]=[CH:21]/[C:22]#[CH:23])=[C:15]([O:32][CH2:33][CH3:34])[N:14]=[C:13]([C:11]([NH:10][CH2:9][C:8]2[CH:35]=[CH:36][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)=[O:12])[CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 86606905HCID 86606905, compound

Product 1

HCID 44419226HCID 44419226, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound from Example 274A (28 mg, 0.05 mmol) in tetrahydrofuran (5 ml) was added tetrabutyl ammonium fluoride (52 mg, 0.2 mmol). The mixture was stirred at room temperature for overnight, and then water and ethyl acetate (20 ml, 1:1) were added. The organic layer was washed with brine and dried over MgSO4. The crude product was purified by reverse phase HPLC (10 mM ammonium acetate, 5% acetonitrile in H2O/CH3CN) to give the titled compound (18.5 mg, 90%). 1H NMR (300 MHz, DMSO-d6) δ ppm 9.02 (t, 1H), 7.87 (d, J=8.14 Hz, 2H), 7.54 (d, J=8.48 Hz, 2H), 7.08 (d, J=16.28 Hz, 1H), 7.04 (s, 1H), 6.57 (s, 2H), 6.48 (dd, J1=16.28, 2.37 Hz, 1H), 4.56 (d, J=6.44 Hz, 2H), 4.46 (q, J=7.01 Hz, 2H), 4.09 (d, J=2.37 Hz, 1H), 3.17 (s, 3H), 1.34 (t, J=7.12 Hz, 3H); MS (APCI) m/z 400 [M+H]+, 398 [M−H]−.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over MgSO4
  3. customThe crude product was purified by reverse phase HPLC (10 mM ammonium acetate, 5% acetonitrile in H2O/CH3CN)

Sources & evidence

ORD record
ord-72b633e8c0444f379dccdc62d625b44c
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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