Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 53893355、化合物

HRID 379658ノート

反応式

HRID 379658 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]([OH:26])([C@H:17]([O:19]C1CCCCO1)[CH3:18])[CH2:11][N:12]1[CH:16]=[N:15][CH:14]=[N:13]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C@:10]([OH:26])([C@H:17]([OH:19])[CH3:18])[CH2:11][N:12]1[CH:16]=[N:15][CH:14]=[N:13]1

参加物

4

反応物 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 9799558HCID 9799558、化合物

生成物 1

HCID 53893355HCID 53893355、化合物収率 63.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
55 °C

実験手順

A mixture of (3R)-2-(2,4,5-trifluorophenyl)-3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (740 mg) and pyridinium p-toluene sulfonate (PPTS, 200 mg) in ethanol (15 ml) was heated at 55° C. for 7 h. The reaction mixture was partitioned between ethyl acetate and water. The water layer was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, and concentrated to dryness in vacuo. Purification of the residue by silica gel chromatography, using dichloromethane:methanol (20:1) as an eluent, gave (2R,3R)-2-(2,4,5-trifluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol (361 mg, 63%) as white amorphous.

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. extractionThe water layer was extracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated to dryness in vacuo
  5. customPurification of the residue by silica gel chromatography

出典と根拠

ORDレコード
ord-6b61015933b345e5991b2a6dd201292a
出典データセット
uspto-grants-2001_10
特許番号
US06300353B1

反応ノート

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