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

HRID 2288106ノート

反応式

HRID 2288106 の反応式
[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]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 27827574-(4-Fluorophenoxy)benzenesulphonyl chlorideHCID 21226206Ethyl acetate hexane2 回HCID 544950714-Aminotetrahydro-2H-pyran-4-carboxylic acid ethyl ester

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.).

後処理

  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)

出典と根拠

ORDレコード
ord-a3744ea56dee4036a1f3c17e86645e4e
出典データセット
uspto-grants-2000_07
特許番号
US06087392

反応ノート

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