Triethylamine → HCID 56770463, 화합물

HRID 221341노트

반응식

HRID 221341 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(OC(Cl)=O)C(C)C.O[NH:29][C:30](=[NH:37])[C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[O:12][N:37]=[C:30]([C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)[N:29]=1)([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 178513374HCID 178513374, 화합물

생성물 1

HCID 56770463HCID 56770463, 화합물

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of tert-butoxycarbonylaminoacetic acid (11.0 g, 5.71 mmol) and triethylamine (802 μl, 5.71 mmol) in toluene (30 ml) was cooled to 0° C. and isobutylchloroformate (740 μl, 5.71 mmol) introduced dropwise. The reaction mixture was stirred at 0° C. for 10 min and at rt for 30 min, whereupon N-hydroxyisonicotinamidine (652 mg, 4.76 mmol) and powdered 3 Å molecular sieves (4 g) were added. After heating under reflux for 12 h the reaction was cooled, filtered through celite and the solvent removed in vacuo. The residue was dissolved in EtOAc (200 ml) and washed with water (30 ml) and saturated aqueous NaHCO3 (30 ml), then dried (MgSO4). The solvent was removed and the residue purified by flash chromatography (IH-EtOAc, 2:3) to afford the title compound: RT=2.97 min; m/z (ES+)=277.1 [M+H]+.

후처리

  1. additionwere added
  2. temperatureAfter heating
  3. temperatureunder reflux for 12 h the reaction
  4. temperaturewas cooled
  5. filtrationfiltered through celite
  6. customthe solvent removed in vacuo
  7. dissolutionThe residue was dissolved in EtOAc (200 ml)
  8. washwashed with water (30 ml) and saturated aqueous NaHCO3 (30 ml)
  9. dry with materialdried (MgSO4)
  10. customThe solvent was removed
  11. customthe residue purified by flash chromatography (IH-EtOAc, 2:3)

출처 및 근거

ORD 기록
ord-5a03f2013d8c40c8b797721547c2b1cb
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207147B2

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