Water → HCID 15232178, compound

HRID 1492519Notes

Reaction equation

HRID 1492519 reaction equation
[NH2:1][CH:2]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[CH2:3][C:4]1[CH:16]=[CH:15][C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1.O>C(Cl)Cl.CO.C(Cl)Cl>[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36]([NH:1][CH:2]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH2:3][C:4]2[CH:16]=[CH:15][C:7]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=2)(=[O:38])=[O:37])=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 18950685HCID 18950685, compound

Product 1

HCID 15232178HCID 15232178, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

In 15 m of methylene chloride were dissolved 0.19 g of ethyl 4-[2-amino-2-(3-pyridyl)ethyl]phenoxyacetate and 0.09 g of triethylamine, followed by addition of 0.17 g of p-toluene sulfonylchloride, and stirred at room temperature for 15 hours. To the reaction mixture was added water, and the organic phase was then separated, which was extracted from aqueous phase with methanol-methylene chloride (5:95 v/v). The organic phases were combined and washed with 2N hydrogen chloride, followed by washing in aqueous saturated sodium chloride solution and drying over magnesium sulfate. Then, the solvent was evaporated off under reduced pressure. The residue obtained was subjected to preparative TLC on silica gel which was developed with methanol-methylene chloride (5:95 v/v). From the band at an Rf value of 0.35 to 0.45, 0.13 g of ethyl 4-[2-(4-toluene sulfonamido)-2-(3-pyridyl)ethyl]phenoxyacetate was obtained, which spectrometric data supports the structure of [18] as follows.

Workup

  1. customthe organic phase was then separated
  2. extractionwhich was extracted from aqueous phase with methanol-methylene chloride (5:95 v/v)
  3. washwashed with 2N hydrogen chloride
  4. washby washing in aqueous saturated sodium chloride solution
  5. dry with materialdrying over magnesium sulfate
  6. customThen, the solvent was evaporated off under reduced pressure
  7. customThe residue obtained

Sources & evidence

ORD record
ord-e8928ac9184d4d9abfe29eac85a22724
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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