Hydrochloric Acid → (E)-3-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile glycineamide

HRID 1488855Notes

Reaction equation

HRID 1488855 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](/[CH:10]=[C:11](\[C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=2)/[C:12]#[N:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C([NH:33][CH2:34][C:35]([NH2:37])=[O:36])(OC(C)(C)C)=O.Cl.O1CCOCC1.C(OCC)C>ClCCl>[NH2:1][C:2]1[CH:3]=[C:4](/[CH:10]=[C:11](\[C:14]2[CH:15]=[C:16]([O:24][CH3:25])[C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=2)/[C:12]#[N:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[NH2:33][CH2:34][C:35]([NH2:37])=[O:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 22877895HCID 22877895, compound

Product 1

HCID 22877843(E)-3-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile glycineamideYield 71.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Eight-hundred milligrams of (E)-3-(3-amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile-Boc-glycineamide were dissolved in 3 ml of dichloromethane, and 3 ml of a solution of 4-M hydrochloric acid and dioxane were added thereto. The mixture was reacted at room temperature for 2 hours. Thirty milliliters of diethyl ether were added thereto, and the resulting mixture was filtered. The thus-obtained powder was hot-washed with a mixture of chloroform, isopropanol and toluene at a ratio by of 6:8:20 to produce 483 mg (1.11 mmols) of the final compound in a yield of 65%.

Workup

  1. customThe mixture was reacted at room temperature for 2 hours
  2. filtrationthe resulting mixture was filtered
  3. washThe thus-obtained powder was hot-washed with a mixture of chloroform, isopropanol and toluene at a ratio by of 6:8:20

Sources & evidence

ORD record
ord-2c28e1936d394b52b6f4aec6725f74e3
Source dataset
uspto-grants-1997_10
Patent number
US05674906

Reaction notes

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