HCID 11135098, compound → HCID 22375877, compound

HRID 1517630Notes

Reaction equation

HRID 1517630 reaction equation
I[CH2:2][O:3][C:4](=[S:10])[O:5][CH:6]([CH2:8][CH3:9])[CH3:7].[CH2:11]([O:18][P:19]([O-:29])([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:4](=[S:10])([O:5][CH:6]([CH2:8][CH3:9])[CH3:7])[O:3][CH2:2][O:29][P:19]([O:18][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]

Participants

4

Reactant 2

HCID 11135098HCID 11135098, compoundHCID 57324724HCID 57324724, compound

Product 1

HCID 22375877HCID 22375877, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product of Example 19B (7.3 g, 27 mmoles) and tetrabutylammonium dibenzylphosphate (13.8 g, 26.6 mmol) were mixed in 20 ml of tetrahydrofuran and stirred at room temperature for 24 hours. The mixture was diluted with 100 mL of tetrahydrofuran, filtered through celite and the solvent was evaporated. The residue was resuspended in 200 mL of 20% ethyl acetate in hexane and the precipitate was filtered and washed with an additional 100 mL of 20% ethyl acetate. The organic filtrates were combined and the solvent was evaporated. Final product was obtained by flash chromatography on silica using 20% ethyl acetate in hexane. Fractions containing product were combined and the solvent was removed to give 8.7 g (78%) of a colorless oil. 1H NMR (300 MHz, CDCl3) δ ppm 0.91 (t, J=7.29 Hz, 3 H) 1.31-1.45 (m, 2 H) 1.55-1.65 (m, 2 H) 2.80-2.90 (m, 2 H) 5.07 (d, J=7.80 Hz, 4 H) 5.65 (d, J=13.90 Hz, 2 H) 7.34 (s, 10 H).

Workup

  1. filtrationfiltered through celite
  2. customthe solvent was evaporated
  3. filtrationthe precipitate was filtered
  4. washwashed with an additional 100 mL of 20% ethyl acetate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-33afe1847e664861b8cdf82a4a56dbd6
Source dataset
uspto-grants-2012_07
Patent number
US08232309B2

Reaction notes

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