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

HRID 1903068Notes

Reaction equation

HRID 1903068 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]#[C:3][CH3:4].[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:3]([CH3:4])=[CH:2][C:1]([O:6][CH3:7])=[O:5]

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 was added 5.0 g (0.055 m) 2,3-dihydroxypropylamine. This solution was heated at 75°-80° for 18 hours and the solvent was then removed at reduced pressure. The residue oil was chromatographed on silica gel, eluting with 10% methanol/chloroform to afford the desired product as a white solid, m.p. 109°-111°. The yield was 5.6 g (59%). ##STR5##

Workup

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

Sources & evidence

ORD record
ord-71d1ec4886934ca2b7b381e9e236be55
Source dataset
uspto-grants-1984_03
Patent number
US04435400

Reaction notes

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