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

HRID 322301

反応式

HRID 322301 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c5da41f8c7294cedace16c22a964aaa3
出典データセット
uspto-grants-2001_04
特許番号
US06211215B1

関連ノート

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