Water → HCID 13251127、化合物

HRID 1912733ノート

反応式

HRID 1912733 の反応式
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:21])[CH2:3]1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.CCOC(C)=O.O>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28]([O:1][C@H:2]2[CH2:19][CH2:18][C@@:17]3([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]4[C@@H:16]3[CH2:15][CH2:14][C@@:12]3([CH3:13])[C@H:8]4[CH2:9][CH2:10][C:11]3=[O:21])[CH2:3]2)(=[O:30])=[O:29])=[CH:24][CH:23]=1

参加物

7

反応物 4

HCID 962WaterHCID 5881DehydroepiandrosteroneHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl Acetate

生成物 1

HCID 13251127HCID 13251127、化合物収率 96%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

実験手順

To a solution of 3β-hydroxyandrost-5-en-17-one (10.00 g) in pyridine (66 mL), toluene-4-sulfonyl chloride (13.20 g) and DMAP (10 mg) were added at 0° C. under stirring. The reaction was allowed to warm to room temperature and stirred for 15 hr. After dilution with EtOAc (300 mL) the mixture was poured into iced water. The organic layer was separated, washed with 1N H2SO4, water and brine, dried and evaporated to dryness to give 3β-(p-toluensulfonyloxy)androst-5-en-17-one (14.70 g, 96%), as a white solid. 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 7.81 (2H, m), 7.48 (2H, m), 5.35 (1H, m), 4.26 (1H, m), 2.46 (3H, s), 2.54-0.93 (19H, m), 1.05 (3H, s), 0.85 (3H, s).

後処理

  1. stirringstirred for 15 hr
  2. customThe organic layer was separated
  3. washwashed with 1N H2SO4, water and brine
  4. customdried
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-cfe8272fc9fa45ea98b649f2831b98cb
出典データセット
uspto-grants-2013_12
特許番号
US08609644B2

反応ノート

読み込み中…