Triethylamine → (3-Ethyl-5-methylisoxazol-4-yl)-carbamic acid 2-trimethylsilanylethyl ester

HRID 2186454ノート

反応式

HRID 2186454 の反応式
[CH2:1]([C:3]1[C:7](C(O)=O)=[C:6]([CH3:11])[O:5][N:4]=1)[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:19])C=CC=CC=1.C([N:31]([CH2:34]C)CC)C.[CH3:36][Si:37]([CH3:42])([CH3:41])[CH2:38][CH2:39][OH:40]>C1(C)C=CC=CC=1>[CH3:36][Si:37]([CH3:42])([CH3:41])[CH2:38][CH2:39][O:40][C:34](=[O:19])[NH:31][C:7]1[C:3]([CH2:1][CH3:2])=[N:4][O:5][C:6]=1[CH3:11]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 180132-(Trimethylsilyl)ethanolHCID 199401P,P-Diphenylphosphinic azideHCID 20633103-Ethyl-5-methyl-1,2-oxazole-4-carboxylic acid

生成物 1

HCID 69838742(3-Ethyl-5-methylisoxazol-4-yl)-carbamic acid 2-trimethylsilanylethyl ester

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

A solution of 3-ethyl-5-methyl-isoxazole-4-carboxylic acid (1.0 g), diphenylphosphoryl azide (1.4 ml) and triethylamine (0.9 ml) in toluene (20 ml) under an atmosphere of nitrogen was heated at 80° C. for 2 hours. 2-(Trimethylsilyl)-ethanol was added dropwise and heating at 80° C. continued for 18 hours. The solvent was removed in vacuo and the residue dissolved in ethyl acetate (100 ml), washed with 1N sodium hydroxide solution (2×25 ml) and washed with brine (25 ml). The organic layer was separated, dried over magnesium sulphate, filtered and the solvent removed in vacuo. Purification by column chromatograhy on silica eluting with 20% ethyl acetate in hexane afforded the title compound as a colourless oil (1.2 g).

後処理

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate (100 ml)
  3. washwashed with 1N sodium hydroxide solution (2×25 ml)
  4. washwashed with brine (25 ml)
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customPurification by column chromatograhy on silica eluting with 20% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-f17d739be8d2414f8f201afcedd72af2
出典データセット
uspto-grants-2002_06
特許番号
US06403791B1

反応ノート

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