1,1'-Carbonyldiimidazole → Methyl 3-(3-benzyl-1,2,4-oxadiazol-5-yl)propanoate

HRID 600594

반응식

HRID 600594 반응식
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][CH2:3][C:4]([O-])=[O:5].C1N=CN(C(N2C=NC=C2)=O)C=1.O/[N:23]=[C:24](\[NH2:32])/[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[CH2:25]([C:24]1[N:32]=[C:4]([CH2:3][CH2:2][C:1]([O:8][CH3:9])=[O:7])[O:5][N:23]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 6930703Mono-Methyl SuccinateHCID 95664652-Phenylacetamidoxime

생성물 1

HCID 59853830Methyl 3-(3-benzyl-1,2,4-oxadiazol-5-yl)propanoate수율 70%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Butanedioic acid, monomethyl ester (4.0 g, 30.3 mmole) and CDI (5.40 g, 33.3 mmole) were dissolved in anhydrous DMF (15 ml) and stirred at room temperature for 3 hours. (1Z)-N′-hydroxy-2-phenylethanimidamide (5.0 g, 33.3 mmole) was added to above solution and the mixture was stirred at 90° C. for 20 hours. The reaction mixture was concentrated and the residue was diluted with water and EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (elution with 1:3 ethyl acetate:hexane) to give the desired product as light yellowish oil (5.2 g, 70% yield). LCMS calculated for C13H15N2O3 (M+H): 247.1. found: 247.1.

후처리

  1. stirringthe mixture was stirred at 90° C. for 20 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionthe residue was diluted with water and EtOAc
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (elution with 1:3 ethyl acetate:hexane)

출처 및 근거

ORD 기록
ord-c0a52cddec654979afd75933b45ab782
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902205B2

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