Isopropanol → HCID 178420765, compound

HRID 1993120Notes

Reaction equation

HRID 1993120 reaction equation
C([O:6][CH2:7][CH3:8])(=O)C(C)O.[CH:9]([OH:12])(C)[CH3:10].F[P-](F)(F)(F)(F)F.[N:20]1([O:29][P+:30](N2CCCC2)(N2CCCC2)N2CCCC2)[C:24]2C=[CH:26][CH:27]=[CH:28][C:23]=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O.CCOC(C)=O>[NH:20]1[CH:26]=[CH:27][CH2:28][CH2:23][CH2:24]1.[PH:30](=[O:29])([O:6][CH2:7][CH3:8])[O:12][CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 7344Ethyl LactateHCID 81531DiisopropylethylamineHCID 2724699PyBOP

Product 1

HCID 178420765HCID 178420765, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 3 (100 mg, 0.120 mmol) in dry dimethylformamide (1 mL) was added Isopropanol (20.0 μL, 0.240 mmol), Benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (135 mg, 0.240 mmol), followed by addition of Diisopropylethylamine (83.0 μL, 0.480 mmol). The mixture was stirred for 14 hours, the resulting residue was diluted in EtOAc, washed with brine (3×) and dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (CH2Cl2/Isopropanol=100/4) to provide 12.2 mg of compound 11: 1H NMR (CDCl3) δ 7.71 (2H, d, J=8.9 Hz), 7.15 (2H, m), 7.0 (2H, m), 6.89 (2H, m), 5.65 (1H, m), 5.03-4.86 (4H, m), 4.34-4.19 (3H, m), 3.89 (3H, s), 3.88 (1H, m), 3.82 (2H, m), 3.65 (4H, m), 3.2-2.9 (11H, m), 2.80 (3H, m) 1.65 (2H, m), 1.86 (1H, m), 1.6 (3H, m), 1.30 (3H, m), 0.92 (6H, m).

Workup

  1. washwashed with brine (3×)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (CH2Cl2/Isopropanol=100/4)

Sources & evidence

ORD record
ord-a702c367afce49b3bbf31f16ba510f32
Source dataset
uspto-grants-2010_01
Patent number
US07649015B2

Reaction notes

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