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

HRID 323797

Reaction equation

HRID 323797 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-394ef33598854287a8a09a224efd90bf
Source dataset
uspto-grants-2001_04
Patent number
US06214872B1

Linked notes

Loading…