tert-Butyl bromoacetate → DI-T-Butyl iminodiacetate

HRID 1397109노트

반응식

HRID 1397109 반응식
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])C(C)(C)C.Br[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>C(#N)C>[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])[CH2:11][NH:1][CH2:2][C:7]([O:9][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:8]

참가 물질

4

반응물 2

HCID 79177tert-Butyl bromoacetateHCID 164608L-tert-Leucine

생성물 1

HCID 4393691DI-T-Butyl iminodiacetate수율 67.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of t-butylglycine (1.40 g, 10.67 mmol) in acetonitrile (20 mL) cooled to 0° C. was added ethyldisopropylamine (1.86 mL, 10.67 mmol) and t-butyl bromoacetate (1.57 mL, 10.67 mmol). The resulting solution was stirred for 24 h at room temperature. The mixture was concentrated to dryness in vacuo, water was added and the solution was extracted with dichloromethane (3×70 mL). The combined organic phases were washed with brine (70 mL), dried over Na2SO4 and concentrated to dryness in vacuo. The crude material was purified by silica gel chromatography (20-80% EtOAc in hexanes) to give the compound 14 (0.88 g, 33.6%). 1H NMR (400 MHz, CDCl3) δ 1.43 (s, 18H), 3.30 (s, 4H).

후처리

  1. concentrationThe mixture was concentrated to dryness in vacuo, water
  2. additionwas added
  3. extractionthe solution was extracted with dichloromethane (3×70 mL)
  4. washThe combined organic phases were washed with brine (70 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness in vacuo
  7. customThe crude material was purified by silica gel chromatography (20-80% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-198517d0fac94c42853f8dbcc2e369df
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901072B2

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