Ethyl Acetate → (5R)-3-[4-(1,1-Dioxo-2,5-dihydrothien-3-yl)-3-fluorophenyl]-5-[4-methyl-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one

HRID 1452568ノート

反応式

HRID 1452568 の反応式
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:19]=[C:18]([CH3:20])[N:17]=[N:16]3)[O:11][C:10]2=[O:21])[CH:5]=[CH:6][C:7]=1I.[O:22]=[S:23]1(=[O:45])[CH2:28][CH:27]=[C:26](C2C(F)=CC(N3C[C@H](CN)OC3=O)=CC=2F)C[CH2:24]1.[F-].[K+].C(OCC)(=O)C>CN1CCCC1=O.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:45]=[S:23]1(=[O:22])[CH2:24][CH:26]=[C:27]([C:7]2[CH:6]=[CH:5][C:4]([N:9]3[CH2:13][C@H:12]([CH2:14][N:15]4[CH:19]=[C:18]([CH3:20])[N:17]=[N:16]4)[O:11][C:10]3=[O:21])=[CH:3][C:2]=2[F:1])[CH2:28]1

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 522689Potassium FluorideHCID 57526977(5S)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3,5-difluorophenyl]-5-(aminomethyl)-oxazolidin-2-oneHCID 58778315(5R)-3-(3-Fluoro-4-iodophenyl)-5-[4-methyl-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one2 回

生成物 1

HCID 57527012(5R)-3-[4-(1,1-Dioxo-2,5-dihydrothien-3-yl)-3-fluorophenyl]-5-[4-methyl-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one収率 10.2%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 13387N-methyl-2-pyrrolidone溶媒2 回

反応条件

温度
40 °C

実験手順

(5R)-3-(3-Fluoro-4-iodophenyl)-5-[4-methyl-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one (Intermediate 13) (200 mg, 0.50 mmol) and copper (I) iodide (39 mg, 0.20 mmol) were dissolved in dry 1-methyl-2-pyrrolidinone (2 ml) and the reaction mixture placed under an atmosphere of argon. TetrakiS(triphenylphosphine)palladium(0) (35 mg, 0.05 mmol) was added, followed by a solution of tributyl(1,1-dioxo-2,5-dihydrothien-3-yl)stannane [Bew, Sean P.; Sweeney, J. B., Synthesis (1994), (7), p698] (263 mg, 0.65 mmol) in 1-methyl-2-pyrrolidinone (2 ml) and the reaction mixture stirred for 5 days at 40° C. Aqueous potassium fluoride 1M (150 ml) and ethyl acetate (150 ml) were added and the insoluble materials filtered off. The ethyl acetate layer was separated, dried over magnesium sulphate, filtered then concentrated in vacuo onto Isolute HM-N (2 g). Purification by chromatography on silica gel with 1.5% methanol in dichloromethane gave 20 mg (10%) of the desired compound.

後処理

  1. filtrationthe insoluble materials filtered off
  2. customThe ethyl acetate layer was separated
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationthen concentrated in vacuo onto Isolute HM-N (2 g)
  6. customPurification by chromatography on silica gel with 1.5% methanol in dichloromethane

出典と根拠

ORDレコード
ord-e2343ad8696141e298fcfb6a70a90c43
出典データセット
uspto-grants-2009_01
特許番号
US07473699B2

反応ノート

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