2,6-Lutidine → HCID 178483623, compound

HRID 967175Notes

Reaction equation

HRID 967175 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:24])[N:10]([CH2:12][CH2:13][C@H:14]2[CH2:19][CH2:18][C@H:17](/[CH:20]=[CH:21]/[CH2:22]O)[CH2:16][CH2:15]2)[CH3:11])=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.CS([Cl:37])(=O)=O>ClCCl.CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:24])[N:10]([CH2:12][CH2:13][C@H:14]2[CH2:19][CH2:18][C@H:17](/[CH:20]=[CH:21]/[CH2:22][Cl:37])[CH2:16][CH2:15]2)[CH3:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 31297Methanesulfonyl chlorideHCID 178483630HCID 178483630, compound

Product 1

HCID 178483623HCID 178483623, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of 135 mg (0.384 mmol) trans-{2-[4-(3-hydroxy-(E)-propenyl)-cyclohexyl]-ethyl}-methyl-carbamic acid 4-chloro-phenyl ester and 0.089 ml (0.77 mmol) 2,6-lutidine in 2 ml of dichloromethane was added under stirring 0.033 ml (0.422 mmol) methane sulfonylchloride. The reaction mixture was stirred for 20 hours at room temperature, then taken up in ether and washed with 1N hydrogen chloride solution and water. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure and the residue then chromatographed on silica gel with a 4:1 v/v mixture of hexane and ethylacetate as the eluent giving 90 mg (63.4%) of trans-{2-[4-(3-chloro-(E)-propenyl)-cyclohexyl]-ethyl}-methyl-carbamic acid 4-chloro-phenyl ester as colorless viscous oil, MS: 370 (MH+, 2 Cl).

Workup

  1. additionwas added
  2. washwashed with 1N hydrogen chloride solution and water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe residue then chromatographed on silica gel with a 4:1 v/v mixture of hexane and ethylacetate as the eluent

Sources & evidence

ORD record
ord-dd51721e86d8494ab6e44b777a82c596
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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