Potassium Carbonate → Methyl-2-(2-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-2-hydroxy-ethylsulfanyl)-benzoate

HRID 512925노트

반응식

HRID 512925 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]4[CH2:22][O:21]4)[CH:15]=3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:23][O:24][C:25](=[O:33])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[SH:32].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(#N)C>[CH3:23][O:24][C:25](=[O:33])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32][CH2:22][CH:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14](/[CH:13]=[CH:12]/[C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=2)[CH:15]=1)[OH:21]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 867207317-Chloro-2-[(E)-2-(3-oxiranyl-phenyl)-vinyl]-quinoline

생성물 1

HCID 86720738Methyl-2-(2-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-2-hydroxy-ethylsulfanyl)-benzoate수율 31.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of epoxide 30 (37 g, 0.120 mol) in a mixture of dimethylformamide (140 ml) and acetonitrile (200 ml) was added methyl-2-mercaptobenzoate (20.0 g, 0.145 mol), followed by addition of anhydrous potassium carbonate (19.8 g, 0.145 mol). The reaction mixture was stirred overnight, filtered and concentrated. The resulting mixture was poured into water (2.0 L), stirred and extracted with ethylacetate (1.0 L). The organic layer was washed with water (500 ml) and brine (500 ml), dried over anhydrous sodium sulphate, evaporated and subjected to FC (EtOAc/hexanes) to afford product as a pale yellow solid 46 (18.0 g, 31% yield).

후처리

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additionThe resulting mixture was poured into water (2.0 L)
  4. stirringstirred
  5. extractionextracted with ethylacetate (1.0 L)
  6. washThe organic layer was washed with water (500 ml) and brine (500 ml)
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated

출처 및 근거

ORD 기록
ord-13a21cd34a534b759ff8f3a5b13453a5
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102665B2

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