Triethylamine → N-(3-isopropoxyphenylacetyl)-N-(2-methoxyethyl)-2-(3,4-dichlorophenyl)-4-mesyloxybutylamine

HRID 1080667Notes

Reaction equation

HRID 1080667 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH:6]([O:9][C:10]1[CH:11]=[C:12]([CH2:16][C:17]([N:19]([CH2:24][CH:25]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=2)[CH2:26][CH2:27][OH:28])[CH2:20][CH2:21][O:22][CH3:23])=[O:18])[CH:13]=[CH:14][CH:15]=1)([CH3:8])[CH3:7].C(N(CC)CC)C>ClCCl>[CH:6]([O:9][C:10]1[CH:11]=[C:12]([CH2:16][C:17]([N:19]([CH2:24][CH:25]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=2)[CH2:26][CH2:27][O:28][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:20][CH2:21][O:22][CH3:23])=[O:18])[CH:13]=[CH:14][CH:15]=1)([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19705329N-(3-isopropoxyphenylacetyl)-N-(2-methoxyethyl)-2-(3,4-dichlorophenyl)-4-hydroxybutylamine

Product 1

HCID 19705331N-(3-isopropoxyphenylacetyl)-N-(2-methoxyethyl)-2-(3,4-dichlorophenyl)-4-mesyloxybutylamineYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.526 g of methanesulfonyl chloride are added to a mixture of 1.8 g of the product obtained in step 4 and 0.46 g of triethylamine in 40 ml of dichloromethane. The reaction mixture is stirred at ambient temperature for 1h and is then concentrated under vacuum. The residue is taken up with ethyl acetate, washed with water, dried over Na2SO4 and concentrated under vacuum to give 2 g of the expected product.

Workup

  1. concentrationis then concentrated under vacuum
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e458732238ee45c5afe72685c907cfb7
Source dataset
uspto-grants-1996_12
Patent number
US05583134

Reaction notes

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