Water → N-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-4-fluoro-phenyl}(thiocarbamoyl)}-beta-alanine, methyl ester

HRID 380791노트

반응식

HRID 380791 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[N:22]=[C:23]=[S:24].Cl.[NH2:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30].C(N(CC)CC)C.O>CC(C)=O.C(Cl)Cl.C(Cl)Cl.C(OCC)C>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[NH:22][C:23]([NH:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[S:24]

참가 물질

8

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 183659632-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl isothiocyanate

생성물 1

HCID 20695541N-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-4-fluoro-phenyl}(thiocarbamoyl)}-beta-alanine, methyl ester수율 74.5%

시약·촉매·용매 3

HCID 180Acetone용매HCID 6344Dichloromethane용매HCID 21881112Ethyl ether methylene chloride용매

실험 절차

A solution of 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl isothiocyanate (6.0 g, 15.8 mmol) and β-alanine, methyl ester, hydrochloride salt (2.65 g, 19.0 mmol) in acetone is cooled to 0° C., treated dropwise with a solution of triethylamine (1.92 g, 19.0 mmol) in methylene chloride, stirred overnight at room temperature, and poured into water. The resultant aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with 5% hydrochloric acid and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a brown foam. Flash column chromatography of the foam using silica gel and a (9:1) methylene chloride/diethyl ether solution gives the title product as an off-white foam (5.68 g, 74.4% yield, mp 110° C.) which is identified by 1H NMR spectral analysis.

후처리

  1. extractionThe resultant aqueous mixture is extracted with ethyl acetate
  2. washwashed sequentially with 5% hydrochloric acid and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a brown foam

출처 및 근거

ORD 기록
ord-55e24b86bf8c46668a51af9ceb402762
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06303783B1

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