Phenacyl bromide → 3-{4-[(4-{[Benzyl(4-phenyl-1,3-thiazol-2-yl)amino]-methyl}benzyl)oxy]phenyl}propanoic acid

HRID 732204

반응식

HRID 732204 반응식
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[CH2:11]([NH:18][C:19]([NH2:21])=[S:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].Cl[CH2:25][C:26]1[CH:45]=[CH:44][C:29]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][C:40]([O:42]C)=[O:41])=[CH:34][CH:33]=2)=[CH:28][CH:27]=1>O.CN(C)C=O>[CH2:11]([N:18]([CH2:25][C:26]1[CH:45]=[CH:44][C:29]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][C:40]([OH:42])=[O:41])=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)[C:19]1[S:20][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:21]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

7

반응물 4

HCID 6259Phenacyl bromideHCID 24758Sodium hydrideHCID 737375N-(Phenylmethyl)thioureaHCID 23082857Methyl 3-(4-([4-(chloromethyl)benzyl]oxy)phenyl)propanoate

생성물 1

HCID 231432423-{4-[(4-{[Benzyl(4-phenyl-1,3-thiazol-2-yl)amino]-methyl}benzyl)oxy]phenyl}propanoic acid수율 41.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

A mixture of 2-bromo-1-phenylethanone (100 mg), N-benzylthiourea (83 mg) and N,N-dimethylformamide (2 mL) was stirred at 80° C. for 1 hr. The reaction mixture was cooled to 0° C., sodium hydride (60% in oil, 80 mg) was added, and the mixture was stirred at room temperature for 30 min. Methyl 3-(4-{[4-(chloromethyl)benzyl]oxy}phenyl)propanoate (300 mg) was added to the reaction mixture at room temperature, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.) and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-1:0 in volume ratio) to give the title compound (110 mg, yield 41%) as colorless crystals.

후처리

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringthe mixture was stirred at room temperature for 30 min
  3. stirringthe mixture was stirred at room temperature for 1 hr
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-1:0 in volume ratio)

출처 및 근거

ORD 기록
ord-a260857e28d7486193734f48abc86e6c
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585880B2

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