Triethylamine → 1-(4'-Fluorobiphenyl-4-sulfonylamino)cyclopentanecarboxylic acid benzyl ester

HRID 1872218

Reaction equation

HRID 1872218 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:41]=[CH:40][C:39]([C:42]2[CH:47]=[CH:46][C:45]([S:48](Cl)(=[O:50])=[O:49])=[CH:44][CH:43]=2)=[CH:38][CH:37]=1>O.O1CCOCC1>[CH2:12]([O:19][C:20]([C:22]1([NH:27][S:48]([C:45]2[CH:44]=[CH:43][C:42]([C:39]3[CH:40]=[CH:41][C:36]([F:35])=[CH:37][CH:38]=3)=[CH:47][CH:46]=2)(=[O:49])=[O:50])[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

6

Reactant 3

HCID 8471TriethylamineHCID 254983Benzyl 1-aminocyclopentanecarboxylate 4-methylbenzenesulfonateHCID 27947494'-Fluorobiphenyl-4-sulfonyl chloride

Product 1

HCID 154800081-(4'-Fluorobiphenyl-4-sulfonylamino)cyclopentanecarboxylic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-aminocyclopentanecarboxylic acid benzyl ester p-toluenesulfonic acid salt (12.1 grams, 30.9 mmol) and triethylamine (10.0 mL, 72 mmol) in water (150 mL) and 1,4-dioxane (150 mL) was added 4'-fluorobiphenyl-4-sulfonyl chloride (8.8 grams, 32.5 mmol). 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 1-(4'-fluorobiphenyl-4-sulfonylamino)cyclopentanecarboxylic acid benzyl ester as a solid, 12.33 grams (76%).

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

Sources & evidence

ORD record
ord-8057c7a85fb74f4fa79730d812f72cd6
Source dataset
uspto-grants-2000_08
Patent number
US06107337

Linked notes

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