Ammonia → Boc-(L)-Pal-NH2

HRID 963948ノート

反応式

HRID 963948 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 54368651Boc-(L)-Pal-NH2収率 75%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
-15 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-633d6029b33347babde579b18916fb75
出典データセット
uspto-grants-1998_06
特許番号
US05766932

反応ノート

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