Palmitoyl chloride → 1-(3-Azido-2,3-dideoxy-5-O-hexadecanoyl-beta-D-erythro-pentofuranosyl)-5-methyl-2(1H)-pyrimidinone

HRID 2248855Notes

Reaction equation

HRID 2248855 reaction equation
[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[N:13][C:12]2=[O:18])[CH2:5]1)=[N+:2]=[N-:3].[C:19](Cl)(=[O:35])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>N1C=CC=CC=1>[N:1]([C@@H:4]1[C@@H:8]([CH2:9][O:10][C:19](=[O:35])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[O:7][C@@H:6]([N:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[N:13][C:12]2=[O:18])[CH2:5]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 8206Palmitoyl chlorideHCID 4515791-(3-Azido-2,3-dideoxy-beta-D-erythropentofuranosyl)-5-methyl-2(1H)-pyrimidinone

Product 1

HCID 867449981-(3-Azido-2,3-dideoxy-5-O-hexadecanoyl-beta-D-erythro-pentofuranosyl)-5-methyl-2(1H)-pyrimidinoneYield 29%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(3-Azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-methyl-2(1H)-pyrimidinone (0.25 g, 1 mMol) was dissolved in 11 mL anhydrous pyridine at 0° C. under a nitrogen atmosphere. Freshly distilled palmitoyl chloride (2.5 mL) was added all at once and the reaction stirred for 2 hrs. The solvents were evaporated away and the residue applied to a silica gel column eluted with 1:6 EtOAc/hexane (v/v). Appropriate fractions were combined and evaporated to give the title compound 0.14 g (0.29 mMol; 29%); mp =65°-67° C.; UV (nm) EtOH: λmax =228 (ε=13400), λmin =212 (ε=10300); 1H NMR (DMSO-d6) δ7.03(d, J=1.37 Hz, 1H, H6), 5.90(dd, J=1.76 Hz, 6.45 Hz, 1H, H1 '), 5.34(s, 1H, H4), 4.50(s, 1H, H3 '), 4.30-4.24(m, 1H, H4 '), 3.93-3.70(m, 2H, H5 '), 2.91(t, J=12.7 Hz, 2H, --C(O)CH2 -- ), 2.57-2.26(m, 2H, H2 '), 1.73(s, 3H, 5-CH3), 1.54-0.80(m, 29 H, palmitoyl).

Workup

  1. customThe solvents were evaporated away
  2. washeluted with 1:6 EtOAc/hexane (v/v)
  3. customevaporated

Sources & evidence

ORD record
ord-d08efde38f0d443aa3cfc4a2007293c5
Source dataset
uspto-grants-1991_08
Patent number
US05041543

Reaction notes

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