Cesium carbonate → (5R)-5-(chloromethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one

HRID 2066806ノート

反応式

HRID 2066806 の反応式
[Cl:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[NH:5][CH2:4]1.Br[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>O1CCOCC1>[Cl:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=2)[CH2:4]1

参加物

6

反応物 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 8170982-Bromo-5-chloropyridineHCID 7058041(5R)-5-(chloromethyl)-1,3-oxazolidin-2-one2 回

生成物 1

HCID 59409863(5R)-5-(chloromethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one収率 59.2%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
85 °C

実験手順

A mixture of (5R)-5-(chloromethyl)-1,3-oxazolidin-2-one (2.15 g, INTERMEDIATE 5), 2-bromo-5-chloropyridine (3.05 g), cesium carbonate (20.67 g), bispalladium tribenzylideneacetone (2.18 g) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (2.07 g) in 16 ml of dioxane was stirred at 85° C. for 12 h. The sample was then cooled to room temperature, and purified was purified via column chromatography (2×) on a Biotage Horizon 65i column eluting with 0% ethyl acetate in hexanes (1 column volume), followed by a gradient to 60% ethyl acetate in hexanes (over 10 column volumes), and held at 60% ethyl acetate for 4 column volumes to provide the title compound (2.32 g, 59%). Mass spectrum (ESI) 249.0 (M+2).

後処理

  1. temperatureThe sample was then cooled to room temperature
  2. custompurified
  3. customwas purified via column chromatography (2×) on a Biotage Horizon 65i column
  4. washeluting with 0% ethyl acetate in hexanes (1 column volume)

出典と根拠

ORDレコード
ord-0da5cc8feee14cd0a4244e17f220b3d8
出典データセット
uspto-grants-2012_10
特許番号
US08293721B2

反応ノート

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