Diazomethane → Methyl 2-((tert-butoxycarbonyl)amino)-5-(trifluoromethyl)benzoate

HRID 1006547노트

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HRID 1006547 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])(C)(C)C.[N+](=C)=[N-]>C1COCC1.CCOCC>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:13][C:14]=1[C:6]([O:5][CH3:1])=[O:7])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 9550DiazomethaneHCID 112307451,1-Dimethylethyl N-[4-(trifluoromethyl)phenyl]carbamateHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 22672049Methyl 2-((tert-butoxycarbonyl)amino)-5-(trifluoromethyl)benzoate수율 159.4%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8028Tetrahydrofuran용매

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온도
-30 °C

실험 절차

4-t-butoxycarbonylaminobenzotrifluoride (3.90 g) was dissolved in THF. At −50° C., t-butyl lithium (30 ml) was added dropwise thereto. The mixture was stirred for 3 hours with keeping at −50° C. Carbon dioxide gas was bubbled into this mixture under stirring (the temperature increased to about −30° C.). The solvent was distilled out. The back-extractration of the residue was 2N NaOH-ether mixture solution was carried out. The aqueous layer was acidified by adding 2N HCl, extracted with ether, washed and dried over. In addition, the layer containing ether was washed, dried over, filtered and concentrated after combining the said layer containing ether to give the crude compound. Such crude compound was dissolved in ether. A solution of diazomethane in ether was added thereto until the reaction solution became yellow. The reaction solution was concentrated and purified on silica gel column chromatography (hexane:AcOEt=20:1→10:1) to give the title compound (3.80 g) having the following physical data.

후처리

  1. customwith keeping at −50° C
  2. customCarbon dioxide gas was bubbled into this mixture
  3. stirringunder stirring (the temperature
  4. distillationThe solvent was distilled out
  5. additionby adding 2N HCl
  6. extractionextracted with ether
  7. washwashed
  8. customdried over
  9. additionIn addition, the layer containing ether
  10. washwas washed
  11. customdried over,
  12. filtrationfiltered
  13. concentrationconcentrated
  14. additioncontaining ether
  15. customto give the crude compound
  16. concentrationThe reaction solution was concentrated
  17. custompurified on silica gel column chromatography (hexane:AcOEt=20:1→10:1)

출처 및 근거

ORD 기록
ord-d0eda1b0d9724c5fbe7b0b02cfc0ba69
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06790866B2

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