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Tris(furan-2-yl)phosphane → N-((5-(4-((4S,5R)-3-(2,2-dichloroacetyl)-4-(fluoromethyl)-2,2-dimethyloxazolidin-5-yl)phenyl)pyridin-2-yl)methyl)-ethanesulfonamide

HRID 1520454
ノート
印刷プレビュー

反応式

HRID 1520454 の反応式
[Cl:1][CH:2]([Cl:24])[C:3]([N:5]1[C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([Sn](C)(C)C)=[CH:14][CH:13]=2)[O:7][C:6]1([CH3:23])[CH3:22])=[O:4].Br[C:26]1[CH:27]=[CH:28][C:29]([CH2:32][NH:33][S:34]([CH2:37][CH3:38])(=[O:36])=[O:35])=[N:30][CH:31]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>CN1CCCC1=O.C(OC(=O)C)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:1][CH:2]([Cl:24])[C:3]([N:5]1[C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([C:26]3[CH:27]=[CH:28][C:29]([CH2:32][NH:33][S:34]([CH2:37][CH3:38])(=[O:35])=[O:36])=[N:30][CH:31]=3)=[CH:14][CH:13]=2)[O:7][C:6]1([CH3:23])[CH3:22])=[O:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 86695409HCID 86695409、化合物HCID 866954112,2-dichloro-1-((4S,5R)-4-(fluoromethyl)-2,2-dimethyl-5-(4-(trimethylstannyl)-phenyl)-oxazolidin-3-yl)ethanone

生成物 1

HCID 86695410N-((5-(4-((4S,5R)-3-(2,2-dichloroacetyl)-4-(fluoromethyl)-2,2-dimethyloxazolidin-5-yl)phenyl)pyridin-2-yl)methyl)-ethanesulfonamide収率 43.1%

試薬・触媒・溶媒 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 8857Ethyl Acetate溶媒
HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
80 °C

実験手順

2,2-dichloro-1-((4S,5R)-4-(fluoromethyl)-2,2-dimethyl-5-(4-(trimethylstannyl)-phenyl)-oxazolidin-3-yl)ethanone (281 mg, 0.66 mmol) and N-((5-bromopyridin-2-yl)methyl)ethanesulfonamide (155 mg, 0.56 mmol) are dissolved in N-Methyl-2-pyrrolidone (40 mL) and purged with nitrogen gas. Pd2(dba)3 (51 mg, 0.055 mmol) and tri-2-furylphosphine (27 mg, 0.11 mmol) are added; the resulting mixture is heated to 80° C. for 18 hours. The reaction mixture is cooled, diluted with ethylacetate, and washed with water. The organic phase is dried (Na2SO4) and concentrated under vacuum. The crude material is chromatographed (24 g Redi-Sep column) eluting from 100% hexanes to 90:10 ethylacetate:hexanes to afford the title compound (125 mg): m/z (Cl) M+H 518.

後処理

  1. custompurged with nitrogen gas
  2. temperatureThe reaction mixture is cooled
  3. washwashed with water
  4. dry with materialThe organic phase is dried (Na2SO4)
  5. concentrationconcentrated under vacuum
  6. customThe crude material is chromatographed (24 g Redi-Sep column)
  7. washeluting from 100% hexanes to 90:10 ethylacetate

出典と根拠

ORDレコード
ord-d6d5d3c8bc58430b9ed3feb98ecd2a79
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09073894B2

反応ノート

読み込み中…

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