Diethyl Ether → (E)-3-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile L-serineamide Hydrochloride

HRID 1488865Notes

Reaction equation

HRID 1488865 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:43][C@H:44]([C:47]([NH2:49])=[O:48])[CH2:45][OH:46])(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.C(OCC)C.C(Cl)(Cl)[Cl:56]>N1CCCCC1>[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:56].[NH2:43][C@H:44]([C:47]([NH2:49])=[O:48])[CH2:45][OH:46]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6212ChloroformHCID 22877902(E)-3-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile Fmoc-L-serineamide

Product 1

HCID 22877911(E)-3-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile L-serineamide HydrochlorideYield 48%

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

(E)-3-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile-Fmoc-L-serineamide (1,430 mg, 2.07 mmols) were dissolved in 5 ml of chloroform and 2 ml of piperidine. The reaction was conducted for 1 hour, and the product was then purified using a silica-gel column (eluent, mixture of ethyl acetate and dichloromethane at a ratio by volume of 1:1). The thus-purified product was concentrated to dryness under reduced pressure, and then dissolved in 10 ml of a solution of 4-M hydrochloric acid and dioxane. The resulting mixture was reacted at 70 ° C. for 1 hour. One-hundred milliliters of diethyl ether were added thereto, and the resulting precipitate was collected by filtration. The thus-obtained powder was purified through medium-pressure liquid chromatography (ODS, mixture of water and acetonitrile at a ratio by volume of from 75:25), and was heat-dissolved in a mixture of chloroform and methanol at a ratio of 5:1 to produce 460 mg (0.992 mmols) of the final product in a yield of 48%.

Workup

  1. customthe product was then purified
  2. additioneluent, mixture of ethyl acetate and dichloromethane at a ratio by volume of 1:1)
  3. concentrationThe thus-purified product was concentrated to dryness under reduced pressure
  4. dissolutiondissolved in 10 ml of a solution of 4-M hydrochloric acid and dioxane
  5. customThe resulting mixture was reacted at 70 ° C. for 1 hour
  6. filtrationthe resulting precipitate was collected by filtration
  7. customThe thus-obtained powder was purified through medium-pressure liquid chromatography (
  8. additionODS, mixture of water and acetonitrile at a ratio by volume of from 75:25), and
  9. dissolutionwas heat-dissolved in a mixture of chloroform and methanol at a ratio of 5:1

Sources & evidence

ORD record
ord-434b2925ded348ed9898320f1c918602
Source dataset
uspto-grants-1997_10
Patent number
US05674906

Reaction notes

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