Water → HCID 18950660, compound

HRID 1492560Notes

Reaction equation

HRID 1492560 reaction equation
[NH2:1][CH:2]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH2:3][CH2:4][C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:6]=1.C(N(CC)CC)C.[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1.O>C(Cl)Cl>[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([S:38]([NH:1][CH:2]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:3][CH2:4][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:16][CH:17]=2)(=[O:40])=[O:39])=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 18950668HCID 18950668, compound

Product 1

HCID 18950660HCID 18950660, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 4-[3-amino-3-(3-pyridyl)propyl]phenoxyacetate (50 mg) and 30 mg of triethylamine were dissolved in 10 ml of methylene chloride, followed by addition of 50 mg of p-chlorobenzene sulfonylchloride, and stirred at room temperature for 2.5 hours. To the reaction mixture was added water, and the organic phase was then separated which was extracted with methanol-methylene chloride (5:95 v/v) from the aqueous phase. The organic phases were combined and washed in saturated aqueous sodium chloride followed by drying over magnesium sulfate and distillation of the solvent. The obtained residue was subjected to chromatography on a silica gel column, and from a fraction eluted with methanol-methylene chloride (5:95 v/v) was obtained 22 mg of ethyl 4-[3-(4-chlorobenzenesulfonamido)-3-(3-pyridyl)propyl]phenoxyacetate. The spectrometric data supports the structure of [38] as follows.

Workup

  1. customthe organic phase was then separated which
  2. extractionwas extracted with methanol-methylene chloride (5:95 v/v) from the aqueous phase
  3. washwashed in saturated aqueous sodium chloride
  4. dry with materialby drying over magnesium sulfate and distillation of the solvent
  5. washfrom a fraction eluted with methanol-methylene chloride (5:95 v/v)

Sources & evidence

ORD record
ord-9919f31f4faf4d88b6df04e704a74541
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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