Water → HCID 67350060, 화합물

HRID 1676353노트

반응식

HRID 1676353 반응식
Cl[C:2](=[O:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[CH2:9]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[CH:10]=[CH2:11].CCN(C(C)C)C(C)C.O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:9]([N:12]([C:13]1[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=1)[C:2](=[O:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5])[CH:10]=[CH2:11]

참가 물질

7

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 123460Methyl malonyl chlorideHCID 11829634N-Allyl-N-(4-fluorophenyl)amine

생성물 1

HCID 67350060HCID 67350060, 화합물수율 92.2%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

Methyl 3-chloro-3-oxopropanoate (9.4 ml, 87 mmol) was added into a solution of N-allyl-4-fluorobenzenamine (12 g, 79 mmol), DIEA (15 ml, 87 mmol) and DMAP (0.97 mg, 7.9 mmol) in CH2Cl2 (200 mL) at 0° C. under nitrogen. The reaction was stirred at 0° C. for 1 hour. The reaction mixture was poured into ice and water, extracted with CH2Cl2, washed with saturated aqueous NaHCO3 and brine. The organic layer was dried with Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (50% EtOAc in hexane) to afford the product (18.3 g, 92% yield) as brown oil. 1H NMR (400 MHz, CDCl3): δ 7.16-7.22 (m, 2H), 7.08-7.12 (m, 2H), 5.80-5.90 (m, 1H), 5.07-5.17 (m, 2H), 4.27-4.32 (m, 2H), 3.67 (s, 3H), 3.20 (s, 2H).

후처리

  1. extractionextracted with CH2Cl2
  2. washwashed with saturated aqueous NaHCO3 and brine
  3. dry with materialThe organic layer was dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (50% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-95b70bbb8539404ea63f0e47de07ef4c
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003662B2

반응 노트

불러오는 중…