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

HRID 2288106노트

반응식

HRID 2288106 반응식
[CH2:1]([O:3][C:4]([C:6]1([NH2:12])[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.[F:20][C:21]1[CH:37]=[CH:36][C:24]([O:25][C:26]2[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=2)=[CH:23][CH:22]=1.C(OCC)(=O)C.CCCCCC>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1([NH:12][S:32]([C:29]2[CH:30]=[CH:31][C:26]([O:25][C:24]3[CH:36]=[CH:37][C:21]([F:20])=[CH:22][CH:23]=3)=[CH:27][CH:28]=2)(=[O:33])=[O:34])[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1)=[O:5])[CH3:2]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 27827574-(4-Fluorophenoxy)benzenesulphonyl chlorideHCID 21226206Ethyl acetate hexane2회HCID 544950714-Aminotetrahydro-2H-pyran-4-carboxylic acid ethyl ester

생성물 1

HCID 544554294-[4-(4-Fluorophenoxy)benzenesulfonylamino]tetrahydropyran-4-carboxylic acid ethyl ester수율 71%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-aminotetrahydropyran-4-carboxylic acid ethyl ester (7.00 grams, 0.0404 mole) in N,N-dimethylformamide (40 mL) was added triethylamine (5.94 mL, 0.043 mole). Solid 4-(4-fluorophenoxy)benzenesulfonyl chloride (12.165 grams, 0.0424 mole) was added in portions. The resulting mixture was stirred at room temperature for 16 hours and then most of the solvent was removed by evaporation under vacuum. The residue was partitioned between saturated sodium bicarbonate solution and dichloromethane. The aqueous layer was extracted with dichloromethane. The combined organic layers were 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 ethyl ester as an amber oil (21.05 grams). 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 ethyl ester as an off-white crystalline solid (12.15 grams, 71%, mp 116-117° C.).

후처리

  1. custommost of the solvent was removed by evaporation under vacuum
  2. customThe residue was partitioned between saturated sodium bicarbonate solution and dichloromethane
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the solvent under vacuum
  7. customprovided crude 4-[4-(4-fluorophenoxy)benzenesulfonylamino]tetrahydropyran-4-carboxylic acid ethyl ester as an amber oil (21.05 grams)

출처 및 근거

ORD 기록
ord-a3744ea56dee4036a1f3c17e86645e4e
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06087392

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