Proton sponge → 3-(3-Methoxy-propoxy)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester

HRID 852639노트

반응식

HRID 852639 반응식
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6]([O:16][CH2:17][CH2:18][CH2:19][OH:20])[CH:5]=1.[CH3:22]N(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.F[B-](F)(F)F.C[O+](C)C>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6]([O:16][CH2:17][CH2:18][CH2:19][O:20][CH3:22])[CH:5]=1

참가 물질

5

반응물 3

HCID 88675Proton sponge2회HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)2회HCID 693569733-(3-Hydroxy-propoxy)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester

생성물 1

HCID 693602353-(3-Methoxy-propoxy)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester수율 58%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3-(3-Hydroxy-propoxy)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (B15) (127 mg, 0.43 mmol, 1 equiv) in CH2Cl2 (2 ml) was treated with proton sponge (279 mg, 1.30 mmol, 3 equiv) and trimethyloxonium tetrafluoroborate (192 mg, 1.30 mmol, 3 equiv). After 3 hrs, further quantities of proton sponge (93 mg, 0.43 mmol, 1 equiv) and trimethyloxonium tetrafluoroborate (65 mg, 0.43 mmol, 1 equiv) were added and stirring was continued for a further 2 h. The mixture was then partitioned between AcOEt and 2N aqueous HCl solution. The two layers were separated and the aqueous phase extracted with AcOEt. The combined organic layers were washed with saturated aqueous NaHCO3 solution, 2N aqueous HCl solution and brine and then dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (ethyl acetate/iso-hexane: 1/4 to 1/3) gave 3-(3-methoxy-propoxy)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (B17) (76 mg, 58%). [M+H]+=308.1

후처리

  1. waitwas continued for a further 2 h
  2. customThe mixture was then partitioned between AcOEt and 2N aqueous HCl solution
  3. customThe two layers were separated
  4. extractionthe aqueous phase extracted with AcOEt
  5. washThe combined organic layers were washed with saturated aqueous NaHCO3 solution, 2N aqueous HCl solution and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica gel (ethyl acetate/iso-hexane: 1/4 to 1/3)

출처 및 근거

ORD 기록
ord-68ab91a83d1243f387007897183ef212
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253198B2

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