Hydrochloric Acid → (3R)-3-{2-[3-chloro-4-(methylsulfonyl)phenyl]-2-(5-(pyridin-2-yl)-1H-pyrrol-2-yl)ethyl}cyclopentanone

HRID 1882077ノート

反応式

HRID 1882077 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([C:35]2[NH:39][C:38]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=3)=[CH:37][CH:36]=2)[CH2:13][C@H:14]2[CH2:34][CH2:33][C:16]3(O[C@H](C4C=CC=CC=4)[C@@H](C4C=CC=CC=4)[O:17]3)[CH2:15]2)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].Cl.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([C:35]2[NH:39][C:38]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=3)=[CH:37][CH:36]=2)[CH2:13][C@H:14]2[CH2:34][CH2:33][C:16](=[O:17])[CH2:15]2)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 593312402-(5-{1-[3-chloro-4-(methylsulfonyl)phenyl]-2-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]ethyl}-1H-pyrrol-2-yl)pyridine

生成物 1

HCID 59331555(3R)-3-{2-[3-chloro-4-(methylsulfonyl)phenyl]-2-(5-(pyridin-2-yl)-1H-pyrrol-2-yl)ethyl}cyclopentanone収率 90%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
55 °C

実験手順

To a solution of 2-(5-{1-[3-chloro-4-(methylsulfonyl)phenyl]-2-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]ethyl}-1H-pyrrol-2-yl)pyridine (580 mg) in tetrahydrofuran (4.5 mL) was added 1M hydrochloric acid (4.5 mL), and the mixture was stirred at 55° C. for 5 hr. After cooling to room temperature, the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution. The reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (360 mg, yield 90%) was obtained as a white amorphous solid from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). MS: 443 (MH+).

後処理

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. dry with materialThe ethyl acetate layer was dried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-131901b98d7146dc9fda10a5bea67feb
出典データセット
uspto-grants-2012_11
特許番号
US08318746B2

反応ノート

読み込み中…