Triethylamine → HCID 21472505, compound

HRID 2294992Notes

Reaction equation

HRID 2294992 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:15][C:14](=[O:16])[O:13][C:11](=[O:12])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].CC[N:19]([CH2:22]C)[CH2:20][CH3:21]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:10][C:11]([N:19]([CH2:20][C:21]2[CH:3]=[CH:4][CH:9]=[CH:10][C:11]=2[O:13][CH3:14])[CH3:22])=[O:12])[CH2:15][C:14]([OH:13])=[O:16])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 543639424-(3,4-Dichlorophenyl)oxane-2,6-dione

Product 1

HCID 21472505HCID 21472505, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Sequentially treat the product of Step 3 (5.9 g) in CH2Cl2 (80 mL) at 0° C. with N-methyl-N-[2-(methoxyphenyl)methyl]amine (3.8 g), Et3N (3.5 mL) and DMAP (278 mg). Stir the mixture at 0° C. for 2 h, allow to warm to room temperature and stir for 20 h. Wash the reaction mixture with 1N HCl (1×100 mL) and brine (1×100 mL), dry the organic layers over MgSO4, filter and concentrate to afford 3,4-dichloro-β-[2-[[(2-methoxy-phenyl)methyl]-methylamino]-2-oxoethyl] benzenepropanoic acid (9.3 g).

Workup

  1. temperatureto warm to room temperature
  2. stirringstir for 20 h
  3. washWash the reaction mixture with 1N HCl (1×100 mL) and brine (1×100 mL)
  4. dry with materialdry the organic layers over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-764953b550134b40b7a6a2d3c7d0eb09
Source dataset
uspto-grants-1997_11
Patent number
US05691362

Reaction notes

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