N,N'-Dimethylethylenediamine → (S)-methyl-3-(5'-fluoro-2,2-dimethyl-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)-5-(2-oxooxazolidin-3-yl)benzoate

HRID 1805361ノート

反応式

HRID 1805361 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C@@:5]12[CH2:13][C:12]1([CH3:15])[CH3:14].[CH3:16][O:17][C:18](=[O:32])[C:19]1[CH:24]=[C:23]([N:25]2[CH2:29][CH2:28][O:27][C:26]2=[O:30])[CH:22]=[C:21](Br)[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>C(#N)C.[Cu]I>[CH3:16][O:17][C:18](=[O:32])[C:19]1[CH:24]=[C:23]([N:25]2[CH2:29][CH2:28][O:27][C:26]2=[O:30])[CH:22]=[C:21]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)[C@@:5]3([CH2:13][C:12]3([CH3:15])[CH3:14])[C:6]2=[O:11])[CH:20]=1

参加物

7

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 67229228Methyl-3-bromo-5-(2-oxooxazolidin-3-yl)benzoateHCID 67230523(S)-5'-fluoro-2,2-dimethylspiro[cyclopropane-1,3'-indolin]-2'-one

生成物 1

HCID 58305358(S)-methyl-3-(5'-fluoro-2,2-dimethyl-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)-5-(2-oxooxazolidin-3-yl)benzoate収率 80%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6342Acetonitrile溶媒

反応条件

温度
90 °C

実験手順

A suspension of (R) and (S)-5′-fluoro-2,2-dimethylspiro[cyclopropane-1,3′-indolin]-2′-one (2 mmol) (prepared as in Example 100), methyl-3-bromo-5-(2-oxooxazolidin-3-yl)benzoate (682 mg, 2 mmol), CuI (76 mg, 0.4 mmol), potassium carbonate (545 mg, 4 mmol) and N,N′-dimethyl-ethane-1,2-diamine (86 uL, 0.8 mmol) in acetonitrile (15 mL) was stirred for 16 hours at 90° C. The precipitate was filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo to afford the title compound as white powder (480 mg, 80%) which was used for the next step without further purification.

後処理

  1. filtrationThe precipitate was filtered off
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-a45b143ce03e4bbd95ca59db818facf5
出典データセット
uspto-grants-2013_01
特許番号
US08354443B2

反応ノート

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