Triethylamine → HCID 23446837, compound

HRID 1841646Notes

Reaction equation

HRID 1841646 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([N:16]([OH:31])[CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]#[CH:28])=[C:21]([O:29][CH3:30])[CH:20]=2)=[O:15])=[CH:9][CH:8]=1.CCN(CC)CC>C(Cl)Cl>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][C:14]([N:16]([O:31][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]#[CH:28])=[C:21]([O:29][CH3:30])[CH:20]=2)=[O:15])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23446811HCID 23446811, compound

Product 1

HCID 23446837HCID 23446837, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.022 ml, 0.286 mmol) is added dropwise to a solution of 2-(4-chloro-phenyl)-N-hydroxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide (0.1 g, 0.26 mmol), and Et3N (0.036 ml, 0.26 mmol) in 1 ml CH2Cl2 at 0° C. The reaction mixture is allowed to warm to room temperature and stirred for another 2 hours. The reaction mixture is then washed with water, 1N HCl, and brine and dried over Na2SO4. After rotary evaporation, the product is purified by flash chromatography (ethyl acetate:hexane, 1:2) to yield 2-(4-chloro-phenyl)-N-mesyloxy-N-[2-(3-methoxy-4-prop-2-ynyloxy-phenyl)-ethyl]-acetamide as a solid, mp. 91-93° C.

Workup

  1. washThe reaction mixture is then washed with water, 1N HCl, and brine
  2. dry with materialdried over Na2SO4
  3. customAfter rotary evaporation
  4. customthe product is purified by flash chromatography (ethyl acetate:hexane, 1:2)

Sources & evidence

ORD record
ord-1c8b7533139648228c34f95995f518aa
Source dataset
uspto-grants-2004_01
Patent number
US06683211B1

Reaction notes

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