Benzyl Bromide → Benzyl 2-(acetylamino)acrylate

HRID 488635

반응식

HRID 488635 반응식
[C:1]([NH:4][C:5](=[CH2:9])[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[C:1]([NH:4][C:5](=[CH2:9])[C:6]([O:8][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:7])(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 794822-Acetamidoacrylic acid

생성물 1

HCID 14382052Benzyl 2-(acetylamino)acrylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 2-acetamidoacrylic acid (10.3 g, 80.0 mmol) and K2CO3 (10 g, 72.5 mmol) in N,N-dimethylformamide (50 mL) was added benzyl bromide (8.7 ml, 72.5 mmol) at room temperature then stirred at room temperature for 3 hours. The mixture was partitioned between ethyl acetate and water (50 mL, 1:1), the aqueous layer was extracted with ethyl acetate (2×45 mL). The combined organic layers was washed with brine (2×25 mL), dried (MgSO4), filtered and concentrated under reduced pressure to provide titled compound. MS (ESI(+)) m/e 220(M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 9.37 (s, 1H), 7.43-7.30 (m, 5H), 6.13 (s, 1H), 5.70 (s, 1H), 5.23 (s, 2H), 2.01 (s, 3H).

후처리

  1. customThe mixture was partitioned between ethyl acetate and water (50 mL, 1:1)
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×45 mL)
  3. washThe combined organic layers was washed with brine (2×25 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b51131c2710a4f8bbe20856230939955
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06972340B2

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