Boron trifluoride etherate → 1-[[4-(4-Fluorophenoxy)benzenesulfonyl]-(3-hydroxypropyl)amino]cyclopentanecarboxylic acid benzyl ester

HRID 323799

반응식

HRID 323799 반응식
[CH2:1]([O:8][C:9]([C:11]1([N:16]([CH2:34][CH2:35][CH2:36][O:37][Si](C(C)(C)C)(C)C)[S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[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.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:1]([O:8][C:9]([C:11]1([N:16]([S:17]([C:20]2[CH:21]=[CH:22][C:23]([O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH2:34][CH2:35][CH2:36][OH:37])[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 8000Boron trifluoride etherateHCID 155242791-{[3-(Tert-butyl-dimethylsilanyloxy)-propyl]-[4-(4-fluorophenoxy)benzenesulfonyl]-amino}cyclopentanecarboxylic acid benzyl ester

생성물 1

HCID 155242801-[[4-(4-Fluorophenoxy)benzenesulfonyl]-(3-hydroxypropyl)amino]cyclopentanecarboxylic acid benzyl ester수율 102.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of the crude 1{[3-(tert-butyl-dimethylsilanyloxy)-propyl]-[4-(4-fluorophenoxy)benzenesulfonyl]-amino}cyclopentanecarboxylic acid benzyl ester (279 grams) in methylene chloride (1 L) at room temperature was added boron trifluoride etherate (103 mL, 0.84 mole). After 1 hour, the reaction was quenched by sequential addition of saturated ammonium chloride solution and water. The organic phase was separated, washed with water and brine and dried over magnesium sulfate. Evaporation of the solvent under vacuum provided crude 1-[[4-(4-fluorophenoxy)benzenesulfonyl]-(3-hydroxypropyl)amino]cyclopentanecarboxylic acid benzyl ester as an amber oil (235 grams).

후처리

  1. customthe reaction was quenched by sequential addition of saturated ammonium chloride solution and water
  2. customThe organic phase was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent under vacuum

출처 및 근거

ORD 기록
ord-47ce682108204cd8b185cbdc6befe9e0
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06214872B1

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