Triethylamine → O-(2-diazo-1,3-dioxobutyl)-N-trifloroacetyl-L-serine

HRID 2165240ノート

反応式

HRID 2165240 の反応式
[C:1]([O:7][CH2:8][C@@H:9]([C:17]([OH:19])=[O:18])[NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].C(N(CC)CC)C.C1(C)C=CC(S([N:36]=[N+:37]=[N-])(=O)=O)=CC=1>C(O)C>[N+:36](=[C:2]([C:3](=[O:4])[CH3:5])[C:1]([O:7][CH2:8][C@@H:9]([C:17]([OH:19])=[O:18])[NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])=[O:6])=[N-:37]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 18640001O-acetoacetyl-N-trifloroacetyl-L-serine

生成物 1

HCID 53767279O-(2-diazo-1,3-dioxobutyl)-N-trifloroacetyl-L-serine収率 76.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

To a solution of O-acetoacetyl-N-trifluoroacetyl-L-serine (232 mg) and triethylamine (0.41 ml) in ethanol (7 ml) was added p-toluenesulfonyl azide (193 mg) at 0° C. The mixture was stirred for an hour at 0° C. and for 4 hours at room temperature. The solvent was distilled off in vacuo and the residue was diluted with chloroform and washed successively with aqueous acetic acid, water and brine. After drying over sodium sulfate, the chloroform extract was filtered and concentrated. The residue was flash chromatographed on silica gel (10 g) eluting successively with chloroform and a 1:9 mixture of methanol and chloroform to give O-(2-diazo-1,3-dioxobutyl)-N-trifloroacetyl-L-serine (193 mg).

後処理

  1. distillationThe solvent was distilled off in vacuo
  2. additionthe residue was diluted with chloroform
  3. washwashed successively with aqueous acetic acid, water and brine
  4. dry with materialAfter drying over sodium sulfate
  5. extractionthe chloroform extract
  6. filtrationwas filtered
  7. concentrationconcentrated
  8. customchromatographed on silica gel (10 g)
  9. washeluting successively with chloroform
  10. additiona 1:9 mixture of methanol and chloroform

出典と根拠

ORDレコード
ord-0f77168854cc4cc39edeae367afea197
出典データセット
uspto-grants-1990_07
特許番号
US04939241

反応ノート

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