Water → 3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethylthio]phenyl]propionic acid

HRID 322301

반응식

HRID 322301 반응식
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[CH2:21][C:22]1[N:23]=[C:24](/[CH:27]=[CH:28]/[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:25][CH:26]=1.O>CN(C)C=O>[C:29]1(/[CH:28]=[CH:27]/[C:24]2[O:25][CH:26]=[C:22]([CH2:21][S:1][C:2]3[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:7]=3)[N:23]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 5797844-Mercaptohydrocinnamic AcidHCID 220097524-Chloromethyl-2-styryl-oxazole

생성물 1

HCID 220096463-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethylthio]phenyl]propionic acid수율 84%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of 3-(4-mercaptophenyl)propionic acid (2.0 g) and triethylamine (2.23 g) in N,N-dimethylformamide (50 ml) was added dropwise a solution of 4-chloromethyl-2-[(E)-2-phenyl ethenyl]oxazole (2.20 g) in N,N-dimethylformamide (10 ml) at 0° C. and then stirred for 2.5 hours. To the reaction mixture was added water, and extracted with diethyl ether. The water layer was made acidic with concentrated hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure to give crystals of 3-[4-[2-[(E)-2-phenyl ethenyl]-4-oxazolylmethylthio]phenyl]propionic acid (3.05 g, 84%). Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 120-121° C.

후처리

  1. extractionextracted with diethyl ether
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c5da41f8c7294cedace16c22a964aaa3
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211215B1

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