Water → HCID 15128663, compound

HRID 580418Notes

Reaction equation

HRID 580418 reaction equation
[CH2:1]([C:4]([CH:13]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-])=O)([C:9]([O:11][CH3:12])=[O:10])[C:5]([O:7][CH3:8])=[O:6])[CH:2]=[CH2:3].O.CO.O>CO>[CH2:1]([C:4]([CH:13]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21])([C:9]([O:11][CH3:12])=[O:10])[C:5]([O:7][CH3:8])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 962WaterHCID 15128648HCID 15128648, compoundHCID 22242641Methanol--water (1/1)

Product 1

HCID 15128663HCID 15128663, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of prepulverized stannous chloride dihydrate (23.82 g, 105.59 mmol) in methanol/concentrated sulfuric acid (318 ml/31.8 ml) at room temperature under a stream of nitrogen was added α-(2-propenyl)-[2-(2-nitrophenyl)--1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester as a solution in 151 ml of methanol. The reaction was run at 40°-58° C. (water bath temperature) for several hours, and then at room temperature overnight. The reaction was quenched by addition of the following reagents in the order specified: Celite, ethyl acetate (389 ml), saturated aqueous potassium carbonate solution (150 ml), and potassium carbonate (101 g), followed by agitation for about 15 minutes. Filtration through two Celite pads (once with a C porosity fritted glass funnel then a D porosity fritted glass funnel) followed by evaporation of the solvents in vacuo yielded a tan oil. Trituration from methanol/water (1 crop) yielded an off-white solid which was recrystallized from methanol (2 crops) to yield 6.87 g of an off-white crystalline solid, melting point 117°-118° C.

Workup

  1. customwas run at 40°-58° C.
  2. customfor several hours
  3. customat room temperature
  4. customovernight
  5. customThe reaction was quenched by addition of the following reagents in the order
  6. filtrationFiltration through two Celite pads (once with a C porosity fritted glass funnel
  7. customa D porosity fritted glass funnel) followed by evaporation of the solvents in vacuo
  8. customyielded a tan oil
  9. customwas recrystallized from methanol (2 crops)

Sources & evidence

ORD record
ord-57f6c2b8f06d4014b0dc15b718a7a521
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

Loading…