Cesium carbonate → N-{5-chloro-2-(oxiran-2-ylmethoxy)-4-[(triisopropylsilyl)oxy]phenyl}-cyclopentanecarboxamide

HRID 270132ノート

反応式

HRID 270132 の反応式
[Cl:1][C:2]1[C:3]([O:17][Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])=[CH:4][C:5]([OH:16])=[C:6]([NH:8][C:9]([CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[N+](C1C=C(S(O[CH2:47][C@@H:48]2[CH2:50][O:49]2)(=O)=O)C=CC=1)([O-])=O>O1CCOCC1>[Cl:1][C:2]1[C:3]([O:17][Si:18]([CH:22]([CH3:24])[CH3:23])([CH:25]([CH3:27])[CH3:26])[CH:19]([CH3:20])[CH3:21])=[CH:4][C:5]([O:16][CH2:47][CH:48]2[CH2:50][O:49]2)=[C:6]([NH:8][C:9]([CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])[CH:7]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 68962023N-{5-chloro-2-hydroxy-4-[(triisopropylsilyl)oxy]phenyl}cyclopentanecarboxamide

生成物 1

HCID 86601494N-{5-chloro-2-(oxiran-2-ylmethoxy)-4-[(triisopropylsilyl)oxy]phenyl}-cyclopentanecarboxamide収率 17.8%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

N-{5-chloro-2-hydroxy-4-[(triisopropylsilyl)oxy]phenyl}cyclopentanecarboxamide (140 mg, 0.3 mmol) was dissolved in 1,4-dioxane (20 mL). Caesium carbonate (170 mg, 0.5 mmol) was added, followed by (2S)-oxiran-2-y-methyl 3-nitrobenzenesulfonate (90 mg, 0.3 mmol). After stirring over night at room temperature the mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and concentrated. Purification by HPLC on C18 (Xterra, 5 um, 19×50 mm; acetonitrile/water 60/40 to 100/0 over 15 min) yielded 25 mg (17%) of the titled intermediate compound.

後処理

  1. customwas partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water
  3. concentrationconcentrated
  4. customPurification by HPLC on C18 (Xterra, 5 um, 19×50 mm; acetonitrile/water 60/40 to 100/0 over 15 min)

出典と根拠

ORDレコード
ord-63fe470f8d1c45e3b81622d5120c734a
出典データセット
uspto-grants-2008_11
特許番号
US07449475B2

反応ノート

読み込み中…