Aniline → 2-(Phenylcarbamoyl)acetic acid

HRID 418567

반응식

HRID 418567 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](Cl)(C)C.CC1(C)[O:19][C:18](=O)[CH2:17][C:16](=[O:21])[O:15]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:19]=[C:18]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:17][C:16]([OH:21])=[O:15]

참가 물질

6

반응물 4

HCID 6115AnilineHCID 6397ChlorotrimethylsilaneHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 516892Sodium Bicarbonate

생성물 1

HCID 2565932-(Phenylcarbamoyl)acetic acid수율 65.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of aniline (13 mL, 143 mmol) in DCM (290 mL) was added TMSCl (18.2 mL, 143 mmol) at room temperature and the reaction mixture was stirred for 1 hour. [Rigo, B.; Fasseur, D.; Cauliez, P. and Couturier, D. Tetrahedron Lett.; 30; 23; 1989; 3073-3076.]. 2,2-Dimethyl-1,3-dioxane-4,6-dione (20.6 g, 143 mmol) was added and combined reaction mixture was stirred overnight at room temperature, poured into saturated NaHCO3 solution and extracted with EtOAc. The aqueous phase was collected, acidified with conc. HCl to pH-3 by addition of 2N HCl and extracted with DCM. The organic phase was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure affording 3-oxo-3-(phenylamino)propanoic acid (1, 16.82 g, 65% yield) as a white solid. MS (m/z): 180.0 (25%) (M+H), 202.0 (100%) (M+Na).

후처리

  1. customreaction mixture
  2. stirringwas stirred overnight at room temperature
  3. extractionextracted with EtOAc
  4. customThe aqueous phase was collected
  5. additionacidified with conc. HCl to pH-3 by addition of 2N HCl
  6. extractionextracted with DCM
  7. dry with materialThe organic phase was dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-baa6e897110f425db32b695f5894c54a
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093264B2

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