Water → 3-[3-(4-Trifluoromethoxy-benzenesulfonylamino)-phenyl]-pyrrolidine-1-carboxylic acid methyl ester

HRID 1260225Notes

Reaction equation

HRID 1260225 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=2)[CH2:6]1)=[O:4].C(N(CC)CC)C.[F:24][C:25]([F:38])([F:37])[O:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.O>C1COCC1>[CH3:1][O:2][C:3]([N:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][S:33]([C:30]3[CH:29]=[CH:28][C:27]([O:26][C:25]([F:24])([F:37])[F:38])=[CH:32][CH:31]=3)(=[O:35])=[O:34])[CH:11]=2)[CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 523102p-(Trifluoromethoxy)benzenesulphonyl chlorideHCID 57470075Methyl 3-(3-aminophenyl)pyrrolidine-1-carboxylate

Product 1

HCID 574944463-[3-(4-Trifluoromethoxy-benzenesulfonylamino)-phenyl]-pyrrolidine-1-carboxylic acid methyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3-amino-phenyl)-pyrrolidine-1-carboxylic acid methyl ester (500 mg, 2.27 mmol) and triethylamine (500 mg, 4.94 mmol) in THF (20 ml) at 10° C. 4-trifluoromethoxy-benzenesulfonylchloride (600 mg, 2.3 mop was added. The mixture was allowed to come to room temperature and was stirred for 16 h. The mixture was poured into water and extracted three times with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, dried over MgSO4 and evaporated under reduced pressure to give the product as a brown oil (1 g, 99%).

Workup

  1. customat 10° C
  2. customto come to room temperature
  3. extractionextracted three times with ethyl acetate
  4. washThe organic layer was washed with water and saturated sodium chloride solution
  5. dry with materialdried over MgSO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-bfa0436de7ae4235bbeccad776cf747e
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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