4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → 2-(4-Carbamoylbenzyl)-3-isopropylmaleic acid dimethyl ester

HRID 418759Notes

Reaction equation

HRID 418759 reaction equation
[CH3:1][O:2][C:3](=[O:23])/[C:4](/[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](O)=[O:21])=[CH:16][CH:15]=1)=[C:5](/[CH:10]([CH3:12])[CH3:11])\[C:6]([O:8][CH3:9])=[O:7].N.O1CCOCC1.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)[N:35]=1.CCCCCC.C(OCC)(=O)C>O1CCCC1>[CH3:1][O:2][C:3](=[O:23])/[C:4](/[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:21])[NH2:35])=[CH:16][CH:15]=1)=[C:5](/[CH:10]([CH3:12])[CH3:11])\[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 21226206Ethyl acetate hexaneHCID 666486782-(4-Carboxybenzyl)-3-isopropylmaleic acid dimethyl esterHCID 66648793Ammonia dioxane

Product 1

HCID 597065082-(4-Carbamoylbenzyl)-3-isopropylmaleic acid dimethyl esterYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-carboxybenzyl)-3-isopropylmaleic acid dimethyl ester (7.8 mg, 0.024 mmol) in tetrahydrofuran (400 μL) were added a 0.5 M ammonia-dioxane solution (600 μL) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (14.8 mg, 0.0535 mmol), and the mixture was stirred at room temperature for 4 h. The reaction mixture was directly concentrated under reduced pressure and the residue thus obtained was subjected to silica gel column chromatography (hexane-ethyl acetate 1:4) to give 7.0 mg of the title compound as a solid (yield: 90%).

Workup

  1. concentrationThe reaction mixture was directly concentrated under reduced pressure
  2. customthe residue thus obtained

Sources & evidence

ORD record
ord-8ae2720606084271942cf932bcad0a47
Source dataset
uspto-grants-2012_01
Patent number
US08093294B2

Reaction notes

Loading…