Tetrabutylammonium Fluoride → HCID 117974671, compound

HRID 1776101Notes

Reaction equation

HRID 1776101 reaction equation
[C:1]([O:5][C:6](=[O:42])[N:7]([C@H:11]1[CH2:19][CH2:18][CH2:17][C@H:16]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[C@@H:15]([O:29][Si](C(C)C)(C(C)C)C(C)C)[C@H:14]([CH3:40])[O:13][C:12]1=[O:41])[CH2:8][O:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:5][C:6](=[O:42])[N:7]([C@H:11]1[CH2:19][CH2:18][CH2:17][C@H:16]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[C@@H:15]([OH:29])[C@H:14]([CH3:40])[O:13][C:12]1=[O:41])[CH2:8][O:9][CH3:10])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 123538160HCID 123538160, compound

Product 1

HCID 117974671HCID 117974671, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a round bottom flask were added tert-butyl((3S,7R,8R,9S)-7-(4-methoxybenzyl)-9-methyl-2-oxo-8-((triisopropylsilyl)oxy)oxonan-3-yl)(methoxymethyl)carbamate (1.61 g, 2.65 mmol), THF (26.5 ml) and TBAF (1.0 M, 5.30 ml, 5.30 mmol) at room temperature and an exotherm noted. The reaction was stirred at room temperature until thin layer chromatography (TLC) showed complete consumption of starting material. After approximately 2 h, the reaction was quenched by the addition of NaHCO3 and extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried over MgSO4, concentrated, and purified by column chromatography on SiO2 (0→10%, hold, 10→20%, hold, 20→50% hold EtOAc/hexanes gradient) to furnish the title product as a colorless oil (703 mg, 59%): IR (neat) 3479, 2976, 2936, 1744, 1700, 1512, 1368, 1297, 1246, 1175 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.15-7.06 (m, 2H), 6.87-6.79 (m, 2H), 4.96-4.87 (m, 1H), 4.85-4.73 (m, 2H), 4.61-4.49 (m, 1H), 4.23-4.18 (m, 1H), 3.79 (s, 3H), 3.51 (td, J=8.8, 5.8 Hz, 1H), 3.32 (d, J=12.9 Hz, 3H), 3.01 (dd, J=13.6, 4.9 Hz, 1H), 2.44 (dd, J=16.2, 7.3 Hz, 1H), 2.07 (d, J=16.5 Hz, 1H), 1.69 (s, 2H), 1.63-1.49 (m, 3H), 1.44 (d, J=5.9 Hz, 9H), 1.40 (d, J=6.3 Hz, 3H), 0.94 (s, 1H); 13C NMR (101 MHz, CDCl3) δ 173.45, 158.00, 129.72, 113.97, 76.28, 55.25, 37.08, 28.24, 27.29, 19.43, 18.18 (Note: Peaks missing, likely due to rotamers); HRMS-ESI (m/z) ([M]+) calcd for C24H37NO7, 451.2558; found, 451.257.

Workup

  1. customconsumption of starting material
  2. customthe reaction was quenched by the addition of NaHCO3
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. custompurified by column chromatography on SiO2 (0→10%, hold, 10→20%, hold, 20→50% hold EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-1b0c80ba505945ba941e1b2b2d7104e9
Source dataset
uspto-grants-2016_02
Patent number
US09265253B2

Reaction notes

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