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

HRID 1488862Notes

Reaction equation

HRID 1488862 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][C@H:34]([C:38]([NH2:40])=[O:39])[C@@H:35]([CH3:37])[OH: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].[NH2:33][C@H:34]([C:38]([NH2:40])=[O:39])[C@@H:35]([CH3:37])[OH:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 22877901HCID 22877901, compound

Product 1

HCID 22877912(E)-3-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile L-threonineamide HydrochlorideYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-3-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile-Boc-L-threonineamide (810 mg, 1.95 mmols) were 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 60° C. for 3 hours. One-hundred milliliters of diethyl ether were added thereto, and the mixture was filtered. The resulting powder was purified twice through medium-pressure liquid chromatography (ODS, mixture of water and acetonitrile at a ratio of 75:25), and was dissolved in a small amount of methanol. A mixture of acetonitrile and ethyl acetate was added thereto, and the precipitate was collected by filtration to obtain 290 mg (0.607 mmols) of the final product in a yield of 31%.

Workup

  1. customThe mixture was reacted at 60° C. for 3 hours
  2. filtrationthe mixture was filtered
  3. customThe resulting powder was purified twice through medium-pressure liquid chromatography (
  4. additionODS, mixture of water and acetonitrile at a ratio of 75:25), and
  5. dissolutionwas dissolved in a small amount of methanol
  6. additionA mixture of acetonitrile and ethyl acetate
  7. additionwas added
  8. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-2b2685f523024f198ef2e8c78489c56b
Source dataset
uspto-grants-1997_10
Patent number
US05674906

Reaction notes

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