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

HRID 1596026
ノート
印刷プレビュー

反応式

HRID 1596026 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6f602153f8114a29a6e76e2a0e2493f5
出典データセット
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06288246B1

反応ノート

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