Iodoethane → 2-Benzyloxycarbonylamino-4-carbamoyl-butyric acid ethyl ester

HRID 2088330

반응식

HRID 2088330 반응식
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:16][CH2:17][C:18](=[O:20])[NH2:19])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[CH2:26](I)[CH3:27]>O>[CH2:26]([O:14][C:13](=[O:15])[CH:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[CH2:16][CH2:17][C:18](=[O:20])[NH2:19])[CH3:27]

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 3024262-(((Benzyloxy)carbonyl)amino)-4-carbamoylbutanoic acidHCID 516892Sodium Bicarbonate

생성물 1

HCID 140366882-Benzyloxycarbonylamino-4-carbamoyl-butyric acid ethyl ester수율 66.9%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of acid (1) (64 g, 0.228 mol), dimeththylformamide (210 ml) and sodium bicarbonate (111 g, 1.32 mol, 5.8 equiv.) was stirred at room temperature for 30 min. Ethyl iodide (34 ml, 66.3 g, 0.425 mol, 1.86 equiv.) was added and stirring was continued overnight under nitrogen. The reaction mixture was slowly diluted with water to 1 L and stirred for 40 min. The solid was collected by filtration, washed well with water and partitioned between ethyl acetate (8 L) and water (3 L). Phases were separated and the aqueous phase was extracted with ethyl acetate (2.5 L). The combined organic extracts were washed with water (1 L), dried over sodium sulfate, stripped and dried in a vacuum oven (50° C.) to produce (2) (47 g, 66.7%).

후처리

  1. stirringstirring
  2. waitwas continued overnight under nitrogen
  3. stirringstirred for 40 min
  4. filtrationThe solid was collected by filtration
  5. washwashed well with water
  6. custompartitioned between ethyl acetate (8 L) and water (3 L)
  7. customPhases were separated
  8. extractionthe aqueous phase was extracted with ethyl acetate (2.5 L)
  9. washThe combined organic extracts were washed with water (1 L)
  10. dry with materialdried over sodium sulfate
  11. customdried in a vacuum oven (50° C.)

출처 및 근거

ORD 기록
ord-979cc2040f5d404dbb3b3238f49b1c41
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08435956B2

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