Ammonia → Boc-(L)-Pal-NH2

HRID 963948노트

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HRID 963948 반응식
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10](O)=[O:11])[CH2:3][C:4]1[CH:9]=[N:8][CH:7]=[CH:6][CH:5]=1.C([N:23](C(C)C)CC)(C)C.C(OC(Cl)=O)C(C)C.N>C(Cl)Cl.C(OCC)(=O)C>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([NH2:23])=[O:11])[CH2:3][C:4]1[CH:9]=[N:8][CH:7]=[CH:6][CH:5]=1

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 62365Isobutyl chloroformateHCID 81531DiisopropylethylamineHCID 7020919Boc-3-(3-pyridyl)-Ala-OH

생성물 1

HCID 54368651Boc-(L)-Pal-NH2수율 75%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
-15 °C

실험 절차

Suspend Boc-(L)-Pal-OH (1.34 g, 5 mmol) in methylene chloride (50 mL) and cool to -15° C. Add diisopropylethylamine (963 μl, 5.5 mmol) and isobutylchloroformate (715 μL, 5.5 mmol). Stir the mixture 15 minutes at -15° C. Pass through the solution a vigorous stream of anhydrous ammonia (over solid sodium hydroxide) for about 3 minutes. Stir the mixture 10 minutes at -15° C. and 20 minutes at room temperature. Evaporate methylene chloride, add ethyl acetate (70 mL) and wash with saturated aqueous solution of sodium bicarbonate. Dry over magnesium sulfate and evaporate. Crystallize from ethyl acetate/hexane to give Boc-(L)-Pal-NH2 (0.98 g, 75%).

후처리

  1. stirringStir the mixture 10 minutes at -15° C.
  2. custom20 minutes
  3. customat room temperature
  4. washwash with saturated aqueous solution of sodium bicarbonate
  5. dry with materialDry over magnesium sulfate
  6. customevaporate
  7. customCrystallize from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-633d6029b33347babde579b18916fb75
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05766932

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