(Oxan-4-yl)methanol → HCID 89875911, compound

HRID 1487088Notes

Reaction equation

HRID 1487088 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[CH2:9]([C:11]1[CH:16]=[CH:15][C:14]([N:17]([CH2:32][CH:33]([CH3:35])[CH3:34])[S:18]([C:21]2[CH:22]=[CH:23][C:24](O)=[C:25]([CH:30]=2)[C:26]([O:28][CH3:29])=[O:27])(=[O:20])=[O:19])=[CH:13][CH:12]=1)[CH3:10].C(P(CCCC)(CCCC)=CC#N)CCC>C1(C)C=CC=CC=1>[CH2:9]([C:11]1[CH:16]=[CH:15][C:14]([N:17]([CH2:32][CH:33]([CH3:34])[CH3:35])[S:18]([C:21]2[CH:22]=[CH:23][C:24]([O:8][CH2:7][CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[C:25]([CH:30]=2)[C:26]([O:28][CH3:29])=[O:27])(=[O:20])=[O:19])=[CH:13][CH:12]=1)[CH3:10]

Participants

5

Reactant 3

HCID 2773573(Oxan-4-yl)methanol2×HCID 4622928Cyanomethylenetributylphosphorane2×HCID 89875692methyl 5-(N-(4-ethylphenyl)-N-isobutylsulfamoyl)-2-hydroxybenzoate

Product 1

HCID 89875911HCID 89875911, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of (tetrahydro-2H-pyran-4-yl)methanol (74.2 mg, 0.639 mmol) and methyl 5-(N-(4-ethylphenyl)-N-isobutylsulfamoyl)-2-hydroxybenzoate (500 mg, 1.277 mmol) in toluene (0.5 mL) at room temperature, was added a solution of 2-(tributylphosphoranylidene)acetonitrile (339 mg, 1.405 mmol) in toluene (0.5 mL) in one charge. The reaction mixture was stirred vigorously for 1 hour, then left to stand overnight. Additional 2-(tributylphosphoranylidene)acetonitrile (339 mg, 1.405 mmol) and (tetrahydro-2H-pyran-4-yl)methanol (74.2 mg, 0.639 mmol) were added and the reaction mixture stirred for an additional 8 hours. The solvent was evaporated in vacuo to give the crude product, which was purified by silica (Si) chromatography (0-100% ethyl acetate-cyclohexane) to give the title compound as an orange gum, 109.6 mg. LCMS [LCMS1] Rt 1.37 min, m/z (ES+) 490 (M+H).

Workup

  1. additioncharge
  2. waitleft
  3. waitto stand overnight
  4. stirringthe reaction mixture stirred for an additional 8 hours
  5. customThe solvent was evaporated in vacuo
  6. customto give the crude product, which
  7. customwas purified by silica (Si) chromatography (0-100% ethyl acetate-cyclohexane)

Sources & evidence

ORD record
ord-3dc756ba8b254765a36d441bc51f13aa
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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