1-[[4-(4-Fluorophenoxy)benzenesulfonyl]-(3-hydroxypropyl)amino]cyclopentanecarboxylic acid benzyl ester → 1{(2-Carboxyethyl)-[4-(4-fluorophenoxy)benzenesulfonyl]amino}cyclopentanecarboxylic acid benzyl ester

HRID 323800

반응식

HRID 323800 반응식
[CH2:1]([O:8][C:9]([C:11]1([N:16]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH2:17][CH2:18][CH2:19][OH:20])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=[O:40].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH2:1]([O:8][C:9]([C:11]1([N:16]([CH2:17][CH2:18][C:19]([OH:40])=[O:20])[S:21]([C:24]2[CH:25]=[CH:26][C:27]([O:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)=[CH:28][CH:29]=2)(=[O:23])=[O:22])[CH2:12][CH2:13][CH2:14][CH2:15]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 155242801-[[4-(4-Fluorophenoxy)benzenesulfonyl]-(3-hydroxypropyl)amino]cyclopentanecarboxylic acid benzyl esterHCID 131709961Jones' reagent

생성물 1

HCID 155242811{(2-Carboxyethyl)-[4-(4-fluorophenoxy)benzenesulfonyl]amino}cyclopentanecarboxylic acid benzyl ester

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A solution of the crude 1-[[4-(4-fluorophenoxy)benzenesulfonyl]-(3-hydroxypropyl)amino]cyclopentanecarboxylic acid benzyl ester (235 grams) in acetone (2 L) was cooled in an ice bath and treated with Jones reagent (about 200 mL) until an orange color persisted. The mixture was stirred from 0° C. to room temperature over 1 hour. After quenching excess oxidant with isopropanol (10 mL), the mixture was filtered and the filtrate was concentrated under vacuum. The residue was taken up in ethyl acetate, washed with water and brine, dried over magnesium sulfate and concentrated to afford a solid which was triturated with a mixture of diethyl ether and hexane to provide 1{(2-carboxyethyl)-[4-(4-fluorophenoxy)benzenesulfonyl]amino}cyclopentane carboxylic acid benzyl ester as a white solid (147 grams).

후처리

  1. customAfter quenching excess oxidant with isopropanol (10 mL)
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated under vacuum
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto afford a solid which
  8. customwas triturated with a mixture of diethyl ether and hexane

출처 및 근거

ORD 기록
ord-5c1863a43715410586d4b550a3f5a458
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06214872B1

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