Potassium Carbonate → 5-{3-[Benzyloxy(2,4,6-trimethoxybenzyl)amino]-3-oxopropyl}-2,2-dimethyl-5-[4-(methoxycarbonyl)phenyl]methyl-[1,3)dioxane-4,6-dione

HRID 1816547Notes

Reaction equation

HRID 1816547 reaction equation
[CH2:1]([O:8][N:9]([CH2:24][C:25]1[C:30]([O:31][CH3:32])=[CH:29][C:28]([O:33][CH3:34])=[CH:27][C:26]=1[O:35][CH3:36])[C:10](=[O:23])[CH2:11][CH2:12][CH:13]1[C:18](=[O:19])[O:17][C:16]([CH3:21])([CH3:20])[O:15][C:14]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:38][C:39]1[CH:48]=[CH:47][C:42]([C:43]([O:45][CH3:46])=[O:44])=[CH:41][CH:40]=1.C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C>[CH2:1]([O:8][N:9]([CH2:24][C:25]1[C:26]([O:35][CH3:36])=[CH:27][C:28]([O:33][CH3:34])=[CH:29][C:30]=1[O:31][CH3:32])[C:10](=[O:23])[CH2:11][CH2:12][C:13]1([CH2:38][C:39]2[CH:40]=[CH:41][C:42]([C:43]([O:45][CH3:46])=[O:44])=[CH:47][CH:48]=2)[C:14](=[O:22])[O:15][C:16]([CH3:21])([CH3:20])[O:17][C:18]1=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 22494961N-benzyloxy-3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-N-(2,4,6-trimethoxybenzyl)-propanamide

Product 1

HCID 224949745-{3-[Benzyloxy(2,4,6-trimethoxybenzyl)amino]-3-oxopropyl}-2,2-dimethyl-5-[4-(methoxycarbonyl)phenyl]methyl-[1,3)dioxane-4,6-dioneYield 78%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To stirring acetonitrile were added N-benzyloxy-3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-N-(2,4,6-trimethoxybenzyl)-propanamide (10.0 g, 19.9 mmol), methyl 4-(bromomethyl)benzoate (5.02 g, 21.9 mmol), potassium carbonate (4.125 g, 29.9 mmol), and benzyltriethylammonium chloride (6.799 g, 29.9 mmol). This reaction mixture was heated to 65° C. for 5 h. The reaction mixture was then allowed to cool and extracted with 100 mL of 10% KHSO4, 50 mL (3 times) of EtOAc, brine and then dried over Na2SO4. The crude product was purified by flash column chromatography (40% EtOAc in hexanes) to give 10.01 g of 5-{3-[benzyloxy(2,4,6-trimethoxybenzyl)amino]-3-oxopropyl}-2,2-dimethyl-5-[4-(methoxycarbonyl)phenyl]methyl-[1,3]dioxane-4,6-dione as a white powder (78% yield).

Workup

  1. temperatureto cool
  2. extractionextracted with 100 mL of 10% KHSO4, 50 mL (3 times) of EtOAc, brine
  3. dry with materialdried over Na2SO4
  4. customThe crude product was purified by flash column chromatography (40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2631a5485ed94ea58342bcce9d407df5
Source dataset
uspto-grants-2005_04
Patent number
US06884907B2

Reaction notes

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