(Oxan-4-yl)methanol → methyl 5-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)-2-((tetrahydro-2H-pyran-4-yl)methoxy)benzoate

HRID 1487075Notes

Reaction equation

HRID 1487075 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:24][CH:25]([CH3:27])[CH3:26])[S:10]([C:13]1[CH:14]=[CH:15][C:16]([OH:23])=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19])(=[O:12])=[O:11].[O:28]1[CH2:33][CH2:32][CH:31]([CH2:34]O)[CH2:30][CH2:29]1.C(P(CCCC)(CCCC)=CC#N)CCC>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:24][CH:25]([CH3:27])[CH3:26])[S:10]([C:13]1[CH:14]=[CH:15][C:16]([O:23][CH2:34][CH:31]2[CH2:32][CH2:33][O:28][CH2:29][CH2:30]2)=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 2773573(Oxan-4-yl)methanolHCID 4622928Cyanomethylenetributylphosphorane2×HCID 89875696methyl 5-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)-2-hydroxybenzoate

Product 1

HCID 72189586methyl 5-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)-2-((tetrahydro-2H-pyran-4-yl)methoxy)benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of methyl 5-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)-2-hydroxybenzoate (100 mg, 0.255 mmol) and (tetrahydro-2H-pyran-4-yl)methanol (29.7 mg, 0.255 mmol) in toluene (1.5 mL) stirred in air at room temperature was added a solution of 2-(tributylphosphoranylidene)acetonitrile (61.7 mg, 0.255 mmol) in toluene (0.5 mL). The reaction mixture was then stirred at 20° C. for 24 hours. After this time, additional 2-(tributylphosphoranylidene)acetonitrile (61.7 mg, 0.255 mmol) was added and the reaction stirred for a further 2 hours. The solvent was evaporated and the purification attempted by mass directed autoprep (ammonium carbonate modifier). The relevant fractions were concentrated under a stream of nitrogen to give a mixture of two products. Further purification was carried out by mass directed autoprep (Method O), to provide the desired product, 25 mg. LCMS [LCMS2] Rt 1.44 min, m/z (ES+) 490 (M+H).

Workup

  1. stirringthe reaction stirred for a further 2 hours
  2. customThe solvent was evaporated
  3. customthe purification
  4. concentrationThe relevant fractions were concentrated under a stream of nitrogen
  5. customto give
  6. additiona mixture of two products
  7. customFurther purification

Sources & evidence

ORD record
ord-ff160ba776b64a77bd3e6cf7327f1a00
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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