Triethylamine → acetic acid 3-{(S)-3-[4-(4-isopropyl-benzenesulfonylamino)-phenyl]-pyrrolidin-1-yl}-propyl ester

HRID 1260242Notes

Reaction equation

HRID 1260242 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]3[CH2:24][CH2:23][NH:22][CH2:21]3)=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[C:32]([O:35][CH2:36][CH2:37][CH2:38]Br)(=[O:34])[CH3:33]>CN(C)C=O.[I-].[Na+]>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]3[CH2:24][CH2:23][N:22]([CH2:38][CH2:37][CH2:36][O:35][C:32](=[O:34])[CH3:33])[CH2:21]3)=[CH:16][CH:15]=2)(=[O:11])=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 122357751-Propanol, 3-bromo-, 1-acetateHCID 574700744-Isopropyl-N-((S)-4-pyrrolidin-3-yl-phenyl)-benzenesulfonamide

Product 1

HCID 53628668acetic acid 3-{(S)-3-[4-(4-isopropyl-benzenesulfonylamino)-phenyl]-pyrrolidin-1-yl}-propyl esterYield 94.3%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

0.21 g of 4-isopropyl-N-[4-((S)-pyrrolidin-3-yl)-phenyl]-benzenesulfonamide (0.62 mmol) were dissolved in 5 ml dimethylformamide. 0.0019 mg of sodium iodide (0.01 mmol) and 0.13 ml of triethylamine (0.94 mmol) were added, followed by addition of 0.136 mg of 3-acetoxy-1-bromo-propane (0.75 mmol). Stirring continued for 15 h at room temperature before the reaction mixture was poured onto 50 ml of crushed ice. The aqueous layer was extracted three times with ethyl acetate and the combined organic phases washed with water and saturated sodium chloride solution. The ethyl acetate phase was dried over magnesium sulfate, filtered, and evaporated to dryness under reduced pressure to yield 0.26 g of the crude product.

Workup

  1. extractionThe aqueous layer was extracted three times with ethyl acetate
  2. washthe combined organic phases washed with water and saturated sodium chloride solution
  3. dry with materialThe ethyl acetate phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b9f7a428b1ec4a5fbad1f1280be657e3
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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