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Benzyl Bromide → (S)-benzyl 2-(dibenzylamino)butanoate

HRID 1025294
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HRID 1025294 반응식
[OH-:1].[Na+].[C:3](=[O:6])([O-])[O-].[K+].[K+].[NH2:9][C@@H:10]([CH2:14][CH3:15])[C:11](O)=O.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O>[CH2:16]([N:9]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@@H:10]([CH2:14][CH3:15])[C:11]([O:6][CH2:3][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:1])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
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참가 물질

6

반응물 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 80283(-)-2-Aminobutyric acid

생성물 1

HCID 57872121(S)-benzyl 2-(dibenzylamino)butanoate

시약·촉매·용매 1

HCID 962Water용매2회

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온도
90 °C

실험 절차

Under an atmosphere of argon, sodium hydroxide (15.5 g, 388 mmol, Eq: 2) and potassium carbonate (53.6 g, 388 mmol, Eq: 2) were combined with water (300 ml) at 0° C. to give a colorless solution. (S)-2-Aminobutanoic acid (20 g, 194 mmol, Eq: 1.00) was added slowly between 0-5° C. The suspension was then heated to 90° C. Then benzyl bromide (133 g, 92.1 ml, 776 mmol, Eq: 4) was added dropwise. The reaction was stirred overnight at 90° C. The reaction mixture was poured into water (300 ml) and extracted with ethyl acetate. The organic layers were dried over Na2SO4 and concentrated in vacuo. The title compound was obtained as a light yellow liquid (84 g, 98.6%, MS (m/e)=374.3 [M+H+]).

후처리

  1. customto give a colorless solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-41b01bff391a4e018e1c90204666cb0d
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08729061B2

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