3-Amino-1,2-propanediol → N-(2',3'-Dihydroxypropyl)-10,12-tricosadiynamide

HRID 865617Notes

Reaction equation

HRID 865617 reaction equation
[C:1]([O:25]C)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[C:11][C:12]#[C:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[NH2:27][CH2:28][CH:29]([OH:32])[CH2:30][OH:31].C[O-].[Na+]>CO>[OH:32][CH:29]([CH2:30][OH:31])[CH2:28][NH:27][C:1](=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[C:11][C:12]#[C:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 735613-Amino-1,2-propanediolHCID 9968876Methyl 10,12-tricosadiynoateHCID 10942334Sodium Methoxide

Product 1

HCID 18688968N-(2',3'-Dihydroxypropyl)-10,12-tricosadiynamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methyl 10,12-tricosadiynoate (1.69 g, 4.67 mmol) was dissolved in methanol. 3-Amino-1,2-propanediol (0.509 g, 5.6 mmol) and sodium methoxide 2.5% solution in methanol (0.146 g, 3 mol %) was added. The mixture was refluxed for 3 hours and the solvent evaporated. The crude product was recrystallized from chloroform. Yield: 1.00 g (51%). 1H NMR (60 MHz, CDCl3): δ 0.7-1.0 (m, 3H, CH3CH2), 1.3 (s, br, 28H, CH2), 2.0-2.4 (m, 6H, CH2), 3.3-3.8 (m, 5H, 2×CH2 +CH (propanediol)), 6.0-6.3 (m, 1H, NH).

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. customthe solvent evaporated
  3. customThe crude product was recrystallized from chloroform

Sources & evidence

ORD record
ord-54a1f4131090497a9912cecc666b2a65
Source dataset
uspto-grants-1996_10
Patent number
US05567413

Reaction notes

Loading…