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

HRID 2276970

反応式

HRID 2276970 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a486a6e8c5624ab3b74c16d1ebf42963
出典データセット
uspto-grants-2015_09
特許番号
US09133104B2

関連ノート

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