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

HRID 1488859Notes

Reaction equation

HRID 1488859 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([N:33]1[CH2:40][CH2:39][CH2:38][C@H:34]1[C:35]([NH2:37])=[O:36])(OC(C)(C)C)=O.[ClH:41].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].[ClH:41].[NH:33]1[CH2:40][CH2:39][CH2:38][C@H:34]1[C:35]([NH2:37])=[O:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 22877900HCID 22877900, compound

Product 1

HCID 22877910(E)-3-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile L-prolineamide HydrochlorideYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-3-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile-Boc-L-prolineamide (1,250 mg, 2.33 mmols) was dissolved in 10 ml of dichloromethane, and 5 ml of a solution of 4-M hydrochloric acid and dioxane were added thereto. The mixture was reacted at room temperature for 1 hour. One-hundred milliliters of diethyl ether were added thereto, and the mixture was filtered. The resulting powder was purified through medium-pressure liquid chromatography (ODS, mixture of water and acetonitrile at a ratio of 70:30). The product was recrystallized three times with a mixture of chloroform and ethyl acetate at a ratio by volume of 1:10 to produce 465 mg (0.980 mmols) of the final product in a yield of 42%.

Workup

  1. customThe mixture was reacted at room temperature for 1 hour
  2. filtrationthe mixture was filtered
  3. customThe resulting powder was purified through medium-pressure liquid chromatography (
  4. additionODS, mixture of water and acetonitrile at a ratio of 70:30)
  5. customThe product was recrystallized three times
  6. additionwith a mixture of chloroform and ethyl acetate at a ratio by volume of 1:10

Sources & evidence

ORD record
ord-57d6d54230a747e0a00e4c7cb6d0944f
Source dataset
uspto-grants-1997_10
Patent number
US05674906

Reaction notes

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