Diethyl Ether → 1-[4-(4-Fluorophenoxy)benzenesulfonylamino]-cyclopentanecarboxylic acid benzyl ester

HRID 323797

반응식

HRID 323797 반응식
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][C:20]([C:22]1([NH2:27])[CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.[F:35][C:36]1[CH:52]=[CH:51][C:39]([O:40][C:41]2[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=2)=[CH:38][CH:37]=1.C(OCC)C>O.COCCOC>[CH2:12]([O:19][C:20]([C:22]1([NH:27][S:47]([C:44]2[CH:45]=[CH:46][C:41]([O:40][C:39]3[CH:51]=[CH:52][C:36]([F:35])=[CH:37][CH:38]=3)=[CH:42][CH:43]=2)(=[O:48])=[O:49])[CH2:23][CH2:24][CH2:25][CH2:26]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 254983Benzyl 1-aminocyclopentanecarboxylate 4-methylbenzenesulfonateHCID 27827574-(4-Fluorophenoxy)benzenesulphonyl chloride

생성물 1

HCID 110051711-[4-(4-Fluorophenoxy)benzenesulfonylamino]-cyclopentanecarboxylic acid benzyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

To a solution of 1-aminocyclopentanecarboxylic acid benzyl ester p-toluenesulfonic acid salt (200 grams, 0.51 mole) and triethylamine (177 mL, 1.27 mole) in water (1 L) and 1,2-dimethoxyethane (1 L) was added 4-(4-fluorophenoxy)benzenesulfonyl-chloride (161 grams, 0.56 moles). The mixture was stirred at room temperature for 16 hours and then most of the solvent was removed by evaporation under vacuum. The mixture was diluted with ethyl acetate and was washed successively with dilute hydrochloric acid solution, water, and brine. The solution was dried over magnesium sulfate and concentrated to leave a brown solid. Trituration with diethyl ether to afforded 1-[4-(4-fluorophenoxy)benzenesulfonylamino]-cyclopentanecarboxylic acid benzyl ester as a tan solid, 167 grams (70%).

후처리

  1. custommost of the solvent was removed by evaporation under vacuum
  2. additionThe mixture was diluted with ethyl acetate
  3. washwas washed successively with dilute hydrochloric acid solution, water, and brine
  4. dry with materialThe solution was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customto leave a brown solid

출처 및 근거

ORD 기록
ord-394ef33598854287a8a09a224efd90bf
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06214872B1

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