Cesium carbonate → HCID 59619302、化合物

HRID 1367524ノート

反応式

HRID 1367524 の反応式
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20](F)=[CH:19][C:18]=3[C:24]([F:27])([F:26])[F:25])(=[O:16])=[O:15])[CH2:11][C@H:10]2[C:28]([N:30]2[CH2:33][C:32]([F:35])([F:34])[CH2:31]2)=[O:29])=[O:8])[CH2:5][CH2:4]1)#[N:2].C(=O)([O-])[O-].[Cs+].[Cs+].[OH:42][CH:43]1[CH2:46][O:45][CH2:44]1>CN(C)C=O>[C:1]([C:3]1([NH:6][C:7]([CH:9]2[CH2:13][CH:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([O:42][CH:43]4[CH2:46][O:45][CH2:44]4)=[CH:19][C:18]=3[C:24]([F:25])([F:26])[F:27])(=[O:15])=[O:16])[CH2:11][CH:10]2[C:28]([N:30]2[CH2:31][C:32]([F:34])([F:35])[CH2:33]2)=[O:29])=[O:8])[CH2:4][CH2:5]1)#[N:2]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 9942117Oxetan-3-olHCID 59619447HCID 59619447、化合物

生成物 1

HCID 59619302HCID 59619302、化合物収率 36.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of (1R,2R,4R)-2-(3,3-Difluoro-azetidine-1-carbonyl)-4-(4-fluoro-2-trifluoromethyl-benzenesulfonyl)-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide (Example 118, 87 mg, 0.16 mmol), cesium carbonate (162 mg, 0.49 mmol) and 3-hydroxyoxetane (35 mg, 0.5 mmol) in N,N-dimethylformamide (3 mL) was stirred at 50° C. for 16 h. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous solution of sodium hydrogenocarbonate. The aqueous layer was extracted with ethyl acetate then the combined organic layers were washed with water and brine then dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with a gradient of dichloromethane/methanol (98:2 v/v) as eluant to afford the title compound (34 mg, 35%) as a white solid. MS (EI): 578.13 (M+H)+.

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic layers were washed with water and brine
  4. dry with materialthen dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel with a gradient of dichloromethane/methanol (98:2 v/v) as eluant

出典と根拠

ORDレコード
ord-9ee07c6932774d88b6a133be32ba7c4b
出典データセット
uspto-grants-2011_02
特許番号
US07893099B2

反応ノート

読み込み中…