Citric Acid → HCID 18414018, compound

HRID 991559Notes

Reaction equation

HRID 991559 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:4]=1[C:5](Cl)=[O:6].Cl.[NH2:15][CH:16]([P:21]([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24])[C:17]([O:19][CH3:20])=[O:18].CN1CCOCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[CH2:26]([O:25][P:21]([O:22][CH2:23][CH3:24])[CH:16]([NH:15][C:5](=[O:6])[C:4]1[C:3]([O:2][CH3:1])=[CH:11][CH:10]=[CH:9][C:8]=1[O:12][CH3:13])[C:17]([O:19][CH3:20])=[O:18])[CH3:27]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 79724-MethylmorpholineHCID 748102,6-Dimethoxybenzoyl chlorideHCID 18414016HCID 18414016, compound

Product 1

HCID 18414018HCID 18414018, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,6-Dimethoxybenzoyl chloride (1.28 g, 6.42 mmol) was added to a mixture of methyl 2-amino-2-(diethoxyphosphino)acetate hydrochloride [1.5 g, 6.11 mmol, prepared by the method of Y. Nasukawa, et al, J. Org. Chem, (1992) 57, 5453] and NMM (1.5 ml, 13.44 mmol) in CH2Cl2 (30 ml). The mixture was stirred overnight at room temperatue then poured into 10% citric acid. The mixture was extracted with CH2Cl2 (×2) and the combined organic extracts washed with sodium hydrogen carbonate solution (×2) and brine, dried (MgSO4) and evaporated in vacuo to give a brown solid (1.62 g). δH (DMSO-d6) 8.82 (1H, dd, J 9.1, 2.5 Hz), 7.29 (1H, t, J 8.4 Hz), 6.65 (2H, d, J 8.4 Hz), 5.20 (1H, dd, J 20.0, 9.2 Hz), 4.15-4.03 (4H, m), 3.72 (3H, s), 3.71 (6H, s), 1.39-1.20 (6H, m); m/z (ESI) 390 (MH+).

Workup

  1. customprepared by the method of Y
  2. extractionThe mixture was extracted with CH2Cl2 (×2)
  3. washthe combined organic extracts washed with sodium hydrogen carbonate solution (×2) and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-52a38ad989a44b37aa0230bdb7111cc0
Source dataset
uspto-grants-2002_10
Patent number
US06465471B1

Reaction notes

Loading…