N-Methoxy-N-methylacetamide → HCID 23589043、化合物

HRID 489720ノート

反応式

HRID 489720 の反応式
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=1[CH3:15])([CH3:4])([CH3:3])[CH3:2].C([Li])(CC)C.CON(C)[C:25](=[O:27])[CH3:26]>O1CCCC1>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=1[CH2:15][C:25](=[O:27])[CH3:26])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 537505N-Methoxy-N-methylacetamideHCID 4935482tert-butyl N-(3-chloro-2-methylphenyl)carbamateHCID 178418400CID 53628100

生成物 1

HCID 23589043HCID 23589043、化合物収率 88.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-10 °C

実験手順

To a cold solution of (3-Chloro-2-methyl-phenyl)-carbamic acid tert-butyl ester (5.0 g, 20.7 mmol) in anhydrous tetrahydrofuran (100 ml) at −40° C. under N2, was added a solution of s-butyl lithium (40 ml, 52 mmol, 1.3 M in cyclohexane) dropwise and maintained the reaction temperature below −30° C. To the bright yellow solution at −50° C. was added a solution of N-methoxy N-methylacetamide (2.33 g, 22.6 mmol) in anhydrous tetrahydrofuran (40 ml) dropwise and maintained the reaction temperature between −50° C. to −40° C. The mixture was allowed to warm to −10° C. over a period of 35 minutes and was then partitioned between diethyl ether and 0.3 N hydrochloric acid solution. The organic extract was washed with water and brine, dried (anhydrous sodium sulfate), and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel eluting with 20% ethyl acetate in hexane to give crude [3-Chloro-2-(2-oxo-propyl)-phenyl]-carbamic acid tert-butyl ester (5.21 g) as a colorless oil.

後処理

  1. temperaturemaintained the reaction temperature below −30° C
  2. temperaturemaintained the reaction temperature between −50° C. to −40° C
  3. customwas then partitioned between diethyl ether and 0.3 N hydrochloric acid solution
  4. extractionThe organic extract
  5. washwas washed with water and brine
  6. dry with materialdried (anhydrous sodium sulfate)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash column chromatography over silica gel eluting with 20% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-bae8508744e9492c9890a54526de86e2
出典データセット
uspto-grants-2005_12
特許番号
US06979696B2

反応ノート

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