Ethyl iodoacetate → Ethyl 2-(4-benzyloxycarbonyl-2-oxopiperazino)acetate

HRID 322015

반응식

HRID 322015 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].I[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:13](=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 12183Ethyl iodoacetateHCID 736777Benzyl 3-oxopiperazine-1-carboxylateHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 22008729Ethyl 2-(4-benzyloxycarbonyl-2-oxopiperazino)acetate수율 81%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-10 °C

실험 절차

To a solution of 4-benyloxycarbonylpiperazin-2-one (M.W.=234.26, 2.34 g, 10 mmol) in anhydrous THF (150 mL) at −78° C. under argon was added lithium bis(trimethylsilyl) amide (1 M in THF, 12 mL, 12 mmol) dropwise. The mixture was stirred at −78° C. for 30 min Ethyl iodoacetate (M.W.−214, 2.14 g, 10 mmol) was added to the mixture at −78° C., stirred, warmed up to −10° C., and then kept in the freezer over night. The reaction was quenched by adding 1N HCl (60 mL) and extracted with EtOAc (200 mL+100 mL). The combined organic layers were washed with sat. NaCl three times, dried with MgSO4, and evaporated to give the crude title compound as a yellowish oil. Reversed-phase HPLC purification afforded the pure compound in 81% yield.

후처리

  1. additionwas added to the mixture at −78° C.
  2. waitkept in the freezer over night
  3. customThe reaction was quenched
  4. additionby adding 1N HCl (60 mL)
  5. extractionextracted with EtOAc (200 mL+100 mL)
  6. washThe combined organic layers were washed with sat. NaCl three times
  7. dry with materialdried with MgSO4
  8. customevaporated

출처 및 근거

ORD 기록
ord-b4ae95728c25488888b6e5953e14300e
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211183B1

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