3-Amino-1,2-propanediol → Methyl 3-[(2,3-dihydroxypropyl)amino]but-2-enoate

HRID 325885

Reaction equation

HRID 325885 reaction equation
[CH3:1][O:2][C:3](=[O:7])[C:4]#[C:5][CH3:6].[OH:8][CH:9]([CH2:12][OH:13])[CH2:10][NH2:11]>C(O)C>[OH:8][CH:9]([CH2:12][OH:13])[CH2:10][NH:11][C:5]([CH3:6])=[CH:4][C:3]([O:2][CH3:1])=[O:7]

Participants

4

Reactant 2

HCID 735613-Amino-1,2-propanediolHCID 141019Methyl but-2-ynoate

Product 1

HCID 71430100Methyl 3-[(2,3-dihydroxypropyl)amino]but-2-enoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 5.0 g (0.051 m) methyl-2-butynoate in 25 ml absolute ethanol is added 5.0 g (0.055 m), 2,3-dihydroxypropylamine. This solution is heated at 75°-80° for 18 hours and the solvent is then removed at reduced pressure. The residue oil is chromatographed on silica gel, eluting with 10% methanol/chloroform to afford the desired product as a white solid. m.p. 109°-111°. The yield is 5.6 g (59%).

Workup

  1. temperatureThis solution is heated at 75°-80° for 18 hours
  2. customthe solvent is then removed at reduced pressure
  3. customThe residue oil is chromatographed on silica gel
  4. washeluting with 10% methanol/chloroform

Sources & evidence

ORD record
ord-403f8c41283f44fd8b08b71a0c0b79aa
Source dataset
uspto-grants-1984_04
Patent number
US04443458

Linked notes

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