3,3-Diethoxypropyne → [1-(5-Diethoxymethyl-isoxazol-3-yl)-3-methyl-butyl]-carbamic acid benzyl ester

HRID 277197ノート

反応式

HRID 277197 の反応式
[CH2:1]([O:8][C:9](=[O:19])[NH:10][CH:11]([CH:16]=[N:17][OH:18])[CH2:12][CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20]([O:22][CH:23]([O:26][CH2:27][CH3:28])[C:24]#[CH:25])[CH3:21]>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:19])[NH:10][CH:11]([C:16]1[CH:25]=[C:24]([CH:23]([O:26][CH2:27][CH3:28])[O:22][CH2:20][CH3:21])[O:18][N:17]=1)[CH2:12][CH:13]([CH3:15])[CH3:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 662853,3-DiethoxypropyneHCID 73456130[1-(Hydroxyimino-methyl)-3-methyl-butyl]-carbamic acid benzyl ester

生成物 1

HCID 18682348[1-(5-Diethoxymethyl-isoxazol-3-yl)-3-methyl-butyl]-carbamic acid benzyl ester収率 52.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of [1-(hydroxyimino-methyl)-3-methyl-butyl]-carbamic acid benzyl ester (1.2 g, 4.5 mmol), 3,3-diethoxy-propyne (1.5 g, 11.4 mmol), CH2Cl2 (40 ml) and TEA (6 drops) was stirred until homogeneous, then Clorox bleach (20 ml) was added. After stirring vigorously for 12 h the layers were separated and the aqueous layer was extracted with CH2Cl2 (3×). The combined organics were dried over Na2SO4; filtered; and concentrated under reduced pressure to give a yellow oil. Purification by Flash 40(small) chromatography eluting with 10% EtOAc in hexanes gave 920 mg of the title compound as a colorless oil. MS [M+1]+391.

後処理

  1. additionwas added
  2. stirringAfter stirring vigorously for 12 h the layers
  3. customwere separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (3×)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationand concentrated under reduced pressure
  8. customto give a yellow oil
  9. customPurification by Flash 40(small) chromatography
  10. washeluting with 10% EtOAc in hexanes

出典と根拠

ORDレコード
ord-8b322dc62cb14c8ca3fdc568761764d3
出典データセット
uspto-grants-2002_03
特許番号
US06355662B1

反応ノート

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