2-{3-[Benzyloxy(2,4,6-trimethoxybenzyl)amino]-3-oxopropyl}-2-(4-carboxyphenyl)methyl-malonic acid → 4-[5-[Benzyloxy(2,4,6-trimethoxybenzyl)amino]-2-carboxy-5-oxopentyl]benzoic acid

HRID 1816549Notes

Reaction equation

HRID 1816549 reaction equation
[CH2:1]([O:8][N:9]([CH2:31][C:32]1[C:37]([O:38][CH3:39])=[CH:36][C:35]([O:40][CH3:41])=[CH:34][C:33]=1[O:42][CH3:43])[C:10](=[O:30])[CH2:11][CH2:12][C:13]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([OH:29])=[O:28])=[CH:23][CH:22]=1)(C(O)=O)[C:14]([OH:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CS(C)=O>[CH2:1]([O:8][N:9]([CH2:31][C:32]1[C:37]([O:38][CH3:39])=[CH:36][C:35]([O:40][CH3:41])=[CH:34][C:33]=1[O:42][CH3:43])[C:10](=[O:30])[CH2:11][CH2:12][CH:13]([C:14]([OH:16])=[O:15])[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]([OH:29])=[O:28])=[CH:25][CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 224949642-{3-[Benzyloxy(2,4,6-trimethoxybenzyl)amino]-3-oxopropyl}-2-(4-carboxyphenyl)methyl-malonic acid

Product 1

HCID 224949584-[5-[Benzyloxy(2,4,6-trimethoxybenzyl)amino]-2-carboxy-5-oxopentyl]benzoic acidYield 71.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

2-{3-[Benzyloxy(2,4,6-trimethoxybenzyl)amino]-3-oxopropyl}-2-(4-carboxyphenyl)methyl-malonic acid (9.30 g, 15.6 mmol ) was taken up in DMSO (10 mL). This solution was heated at 130° C. for 1.5 h. The reaction mixture was then allowed to come to room temperature. The solvent was then removed under reduced pressure. EtOAc was used as an azeotrope to remove the DMSO. The residue was partitioned between 50 mL of 10% KHSO4 and 100 mL of EtOAc. The organic layer was washed with brine (50 mL), dried over Na2SO4, and concentrated to give 6.17 g of 4-[5-[benzyloxy(2,4,6-trimethoxybenzyl)amino]-2-carboxy-5-oxopentyl]benzoic acid as an off white powder (76% yield). 1H NMR (CDCl3): d 0.88-0.96 (m, 2H), 1.26-1.91 (m, 2H), 2.02-2.32 (m,2H), 2.47-2.83 (m, 2H), 3.01-3.60 (m,2H), 4.70 (s, 1H), 7.14-7.29 (m,9H), 7.93-7.96 (d, 2H).

Workup

  1. customto come to room temperature
  2. customThe solvent was then removed under reduced pressure
  3. customto remove the DMSO
  4. customThe residue was partitioned between 50 mL of 10% KHSO4 and 100 mL of EtOAc
  5. washThe organic layer was washed with brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9a650e485c274b86a76ba6553d8ef24e
Source dataset
uspto-grants-2005_04
Patent number
US06884907B2

Reaction notes

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