Triethylamine → HCID 18625877, compound

HRID 1859952Notes

Reaction equation

HRID 1859952 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[OH:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH:24]([CH2:30][CH2:31][O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19][CH:18]=1>ClCCl>[CH3:8][S:9]([O:13][CH2:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:23][CH:24]([CH2:30][CH2:31][O:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][CH:22]=1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18625804HCID 18625804, compound

Product 1

HCID 18625877HCID 18625877, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.29 ml) and methanesulfonyl chloride (0.12 ml) were added to a solution of ethyl 3-[4-(2-hydroxyethoxy)phenyl]-2-(2-phenoxyethyl)propionate (503 mg), which is the product of Reference example 3(f), in anhydrous dichloromethane (10 ml). The reaction mixture was stirred at ambient temperature for 2 hours. At the end of this time the reaction mixture was concentrated. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate and then concentrated. The residue was purified via chromatography on silica gel column using hexane/ethyl acetate=2/1-3/2 as the eluant to afford the desired compound (632 mg) as a syrup.

Workup

  1. concentrationAt the end of this time the reaction mixture was concentrated
  2. customThe residue was partitioned between ethyl acetate and water
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified via chromatography on silica gel column

Sources & evidence

ORD record
ord-e5391c8f2efd46b0ab8c7c5e8816c322
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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