N,N,N',N'-Tetramethylethylenediamine → Methyl 3-((tert-butoxycarbonyl)amino)furan-2-carboxylate

HRID 390809

반응식

HRID 390809 반응식
[O:1]1[CH:5]=[CH:4][C:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:2]1.CN(CCN(C)C)C.C([Li])CCC.[C:27](=O)([O:30]C)[O:28][CH3:29]>C1COCC1>[CH3:29][O:28][C:27]([C:2]1[O:1][CH:5]=[CH:4][C:3]=1[NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[O:30]

참가 물질

6

반응물 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 12021Dimethyl CarbonateHCID 12207186tert-butyl N-(furan-3-yl)carbamateHCID 178418339Butyllithium

생성물 1

HCID 52987670Methyl 3-((tert-butoxycarbonyl)amino)furan-2-carboxylate수율 51%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a solution of tert-butyl furan-3-ylcarbamate 32 (1.7 g, 1.0 eq) in THF (50 ml) at −30° C. was added TMEDA (1.75 ml, 1.3 eq) followed by 1.6M solution of n-butyllithium (8.4 ml, 2.25 eq, 1.6M in hexanes). Reaction mixture was allowed to warm up to 0° C. and stirred for 1 h, before being cooled back to −30° C. Dimethyl carbonate (2.4 ml, 3.0 eq) was quickly added, before the reaction mixture was allowed to warm up to room temperature for 1 hr. Reaction mixture was quenched with 2M HCl, followed by addition of saturated aq. NaCl. Mixture was extracted with ethyl acetate. The combined organic extracts were dried with Na2SO4 and concentrated. The crude reaction mixture was purified by flash chromatography to yield tert-butyl 2-(methoxycarbonyl)furan-3-ylcarbamate 33 (1.14 g, 51%): MS (Q1) 242 (M)+.

후처리

  1. customReaction mixture
  2. temperaturebefore being cooled back to −30° C
  3. temperatureto warm up to room temperature for 1 hr
  4. customReaction mixture
  5. customwas quenched with 2M HCl
  6. additionfollowed by addition of saturated aq. NaCl
  7. extractionMixture was extracted with ethyl acetate
  8. dry with materialThe combined organic extracts were dried with Na2SO4
  9. concentrationconcentrated
  10. customThe crude reaction mixture
  11. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-fb3a4c3755864f2c88bff16ca71e6767
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383620B2

연결된 노트

불러오는 중…