3-Aminobutanamide → 1-[p-(2-Methoxycarbonylaminovinyl)-phenoxy]-2-hydroxy-3-(2-carbamoyl-1-methyl-ethylamino)-propane

HRID 259605Notes

Reaction equation

HRID 259605 reaction equation
[CH3:1][O:2][C:3]([NH:5][CH:6]=[CH:7][C:8]1[CH:18]=[CH:17][C:11]([O:12][CH2:13][CH:14]2[O:16][CH2:15]2)=[CH:10][CH:9]=1)=[O:4].[NH2:19][CH:20]([CH3:25])[CH2:21][C:22]([NH2:24])=[O:23]>C(#N)C>[CH3:1][O:2][C:3]([NH:5][CH:6]=[CH:7][C:8]1[CH:18]=[CH:17][C:11]([O:12][CH2:13][CH:14]([OH:16])[CH2:15][NH:19][CH:20]([CH3:25])[CH2:21][C:22](=[O:23])[NH2:24])=[CH:10][CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 109313813-AminobutanamideHCID 543618201-[p-(2-Methoxycarbonylaminovinyl)-phenoxy]-2,3-epoxypropane

Product 1

HCID 544044191-[p-(2-Methoxycarbonylaminovinyl)-phenoxy]-2-hydroxy-3-(2-carbamoyl-1-methyl-ethylamino)-propane

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

7.5 g (0.03 mol) of 1-[p-(2-methoxycarbonylaminovinyl)-phenoxy]-2,3-epoxypropane are dissolved in 75 ml of acetonitrile and added dropwise to a boiling stirred solution of 3.34 g (0.029 mol) of β-aminobutyric acid amide in 75 ml of acetonitrile. The mixture is stirred for 20 hours under reflux, the solvent is removed by distillation under reduced pressure and the oil which remains is partitioned between 350 ml of 0.1 N hydrochloric acid and 300 ml of ethyl acetate. The hydrochloric acid extract is separated off, rendered alkaline with sodium carbonate and extracted four times with 100 ml of ethyl acetate at a time. The organic phases are dried over sodium sulphate and evaporated under reduced pressure. The resulting oil yields 1-[p-(2-methoxycarbonylaminovinyl)-phenoxy]-2-hydroxy-3-(2-carbamoyl-1-methyl-ethylamino)-propane, of melting point 109°-111° C., from acetone-ethyl acetate.

Workup

  1. additionadded dropwise to a boiling
  2. temperatureunder reflux
  3. customthe solvent is removed by distillation under reduced pressure
  4. customthe oil which remains is partitioned between 350 ml of 0.1 N hydrochloric acid and 300 ml of ethyl acetate
  5. extractionThe hydrochloric acid extract
  6. customis separated off
  7. extractionextracted four times with 100 ml of ethyl acetate at a time
  8. dry with materialThe organic phases are dried over sodium sulphate
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d52a38ae1a4a44f182182569b9798a20
Source dataset
uspto-grants-1977_07
Patent number
US04038414

Reaction notes

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