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 380791ノート

反応式

HRID 380791 の反応式
[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]

参加物

8

反応物 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

生成物 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 ester収率 74.5%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 6344Dichloromethane溶媒HCID 21881112Ethyl ether methylene chloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-55e24b86bf8c46668a51af9ceb402762
出典データセット
uspto-grants-2001_10
特許番号
US06303783B1

反応ノート

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