Triethylamine → 4-[4-(4-Fluorophenoxy)benzenesulfonylamino]tetrahydropyran-4-carboxylic acid benzyl ester

HRID 1976911Notes

Reaction equation

HRID 1976911 reaction equation
[CH2:1]([O:8][C:9]([C:11]1([NH2:17])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:25][C:26]1[CH:42]=[CH:41][C:29]([O:30][C:31]2[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=2)=[CH:28][CH:27]=1.C(OCC)(=O)C.CCCCCC>CN(C)C=O>[CH2:1]([O:8][C:9]([C:11]1([NH:17][S:37]([C:34]2[CH:35]=[CH:36][C:31]([O:30][C:29]3[CH:41]=[CH:42][C:26]([F:25])=[CH:27][CH:28]=3)=[CH:32][CH:33]=2)(=[O:38])=[O:39])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27827574-(4-Fluorophenoxy)benzenesulphonyl chlorideHCID 21226206Ethyl acetate hexane2×HCID 539944184-Aminotetrahydropyran-4-carboxylic acid benzyl ester

Product 1

HCID 538527694-[4-(4-Fluorophenoxy)benzenesulfonylamino]tetrahydropyran-4-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-aminotetrahydropyran-4-carboxylic acid benzyl ester (0.0404 mole) in N,N-dimethylformamide (40 mL) is added triethylamine (5.94 mL, 0.043 mole). Solid 4-(4-fluorophenoxy)benzenesulfonyl chloride (12.165 grams, 0.0424 mole) is added to the above solution in portions. The resulting mixture is stirred at room temperature for 16 hours and then most of the solvent is removed by evaporation under vacuum. The residue was partitioned between saturated sodium bicarbonate solution and dichloromethane. The aqueous layer is separated and extracted with dichloromethane. The combined organic layers are washed with brine and dried over sodium sulfate. Evaporation of the solvent under vacuum provided crude 4-[4-(4-fluorophenoxy)benzenesulfonylamino]tetrahydropyran-4-carboxylic acid benzyl ester. Flash chromatography on silica gel eluting with 25% ethyl acetate/hexane followed by 50% ethyl acetate/hexane provided 4-[4-(4-fluorophenoxy)benzenesulfonylamino]tetrahydropyran-4-carboxylic acid benzyl ester.

Workup

  1. custommost of the solvent is removed by evaporation under vacuum
  2. customThe residue was partitioned between saturated sodium bicarbonate solution and dichloromethane
  3. customThe aqueous layer is separated
  4. extractionextracted with dichloromethane
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over sodium sulfate
  7. customEvaporation of the solvent under vacuum
  8. customprovided crude 4-[4-(4-fluorophenoxy)benzenesulfonylamino]tetrahydropyran-4-carboxylic acid benzyl ester

Sources & evidence

ORD record
ord-3659b75d226148b28ce464381c2ffe67
Source dataset
uspto-grants-2001_05
Patent number
US06229025B1

Reaction notes

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