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Methyl chloroformate → Carbonic acid 3-(2,5-dimethyl-phenyl)-8-methoxy-2-oxo-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester methyl ester

HRID 1962361
ノート
印刷プレビュー

反応式

HRID 1962361 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]1[C:10](=[O:22])[NH:11][C:12]2([CH2:19][CH2:18][N:17]([O:20][CH3:21])[CH2:16][CH2:15]2)[C:13]=1[OH:14].C(N(C(C)C)C(C)C)C.Cl[C:33]([O:35][CH3:36])=[O:34]>ClC1C=CC=CC=1>[CH3:36][O:35][C:33](=[O:34])[O:14][C:13]1[C:12]2([CH2:19][CH2:18][N:17]([O:20][CH3:21])[CH2:16][CH2:15]2)[NH:11][C:10](=[O:22])[C:9]=1[C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[CH3:1]
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

5

反応物 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 547422463-(2,5-Dimethyl-phenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one

生成物 1

HCID 44603930Carbonic acid 3-(2,5-dimethyl-phenyl)-8-methoxy-2-oxo-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester methyl ester

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒3 回

反応条件

温度
50 °C

実験手順

To a solution of 200 mg of 3-(2,5-dimethyl-phenyl)-4-hydroxy-8-methoxy-1,8-diaza-spiro[4.5]dec-3-en-2-one and 0.14 ml of ethyl diisopropyl amine in 2 ml of chlorobenzene was added a solution of 66 mg of methyl chloroformate in 0.5 ml of chlorobenzene at 50° C. After stirring for 1 hour at 50° C., the reaction mixture was cooled to room temperature, diluted with 5 ml of chlorobenzene and washed with cold 5% aqueous sodium hydroxide and water. The organic phase was separated, dried over sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel. Yield: 120 mg of carbonic acid 3-(2,5-dimethyl-phenyl)-8-methoxy-2-oxo-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester methyl ester (title compound A1). This material was triturated with ethyl acetate/hexane, filtered and dried to afford a solid, mp: 186-188° C.

後処理

  1. temperaturethe reaction mixture was cooled to room temperature
  2. washwashed with cold 5% aqueous sodium hydroxide and water
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography on silica gel
  8. customThis material was triturated with ethyl acetate/hexane
  9. filtrationfiltered
  10. customdried
  11. customto afford a solid, mp: 186-188° C.

出典と根拠

ORDレコード
ord-b57516b3cc474a2e9c2572dd222ecfd2
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08415369B2

反応ノート

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