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

HRID 2165240노트

반응식

HRID 2165240 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0f77168854cc4cc39edeae367afea197
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04939241

반응 노트

불러오는 중…