Cyclopentanol → (S)-(4-Nitro-benzenesulfonylamino)-phenyl-acetic acid cyclopentyl ester

HRID 2360625

반응식

HRID 2360625 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C@@H:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([OH:17])=[O:16])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.[CH:28]1(O)[CH2:32][CH2:31][CH2:30][CH2:29]1>>[CH:28]1([O:16][C:15](=[O:17])[C@@H:14]([NH:13][S:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)(=[O:12])=[O:11])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:32][CH2:31][CH2:30][CH2:29]1

참가 물질

4

반응물 3

HCID 7298CyclopentanolHCID 24386Thionyl ChlorideHCID 362697(s)-(4-Nitro-benzenesulfonylamino)-phenyl-acetic acid

생성물 1

HCID 57971706(S)-(4-Nitro-benzenesulfonylamino)-phenyl-acetic acid cyclopentyl ester수율 70%

반응 조건

온도
70 °C

실험 절차

To a solution of stage 1 acid (4.32 g, 12.8 mmol) in cyclopentanol (60 ml) at 0° C. was added slowly thionyl chloride (9.3 ml, 128 mmol). The reaction mixture was stirred and heated under reflux at 70° C. for 2 hours. The excess thionyl chloride was removed by evaporation in vacuo, the reaction mixture was extracted into EtOAc and washed with saturated NaHCO3 solution and dried over Na2SO4, filtered and evaporated to dryness. Flash column chromatography purification with DCM gave the required product (3.6 g, 70% yield). LCMS purity of 100%, (molecular ion not observed).

후처리

  1. temperatureheated
  2. customThe excess thionyl chloride was removed by evaporation in vacuo
  3. extractionthe reaction mixture was extracted into EtOAc
  4. washwashed with saturated NaHCO3 solution
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customFlash column chromatography purification with DCM

출처 및 근거

ORD 기록
ord-d08be99f95534bc494d2e184f144f70a
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08686032B2

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