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

HRID 2186454노트

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HRID 2186454 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f17d739be8d2414f8f201afcedd72af2
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06403791B1

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