Sodium hydride → HCID 178525416, compound

HRID 1608755Notes

Reaction equation

HRID 1608755 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[N:6][N:5]=[N:4]1.I[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21]>CN(C=O)C>[NH:3]1[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[N:6][N:5]=[N:4]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 37919712-Iodododecanoic acidHCID 178418441HCID 178418441, compound

Product 1

HCID 178525416HCID 178525416, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of NaH (0.045 g, 80% suspension in oil) in DMF (1 ml) was added to a solution of tetrazole 44 (0.095 g, 1.35 mmmol) in DMF (1 ml). After stirring the reactants for 15 min, a solution of 12-iodo-dodecanoic acid 45 (0.2 g, 0.6 mmol) was added. The resulting mixture was stirred at room temperature for 1 h and at 55° C. for 1.5 h and then concentrated in vacuo. The residue was treated with 1N HCl(5 ml) and extracted with EtOAc (2×10 ml). The organic layer was washed with water, dried (Na2SO4), concentrated under reduced pressure and the residue was crystallized from EtOAc/Hexane to give the title compound 46 (0.095 g, 26%) as a 1:3 mixture of N-3 and N-1 isomers, respectively. This mixture was tested directly as a substrate for NMT. 1H NMR (CDCl3) δ: 8.59 and 8.5 (2s, 1H); 4.65 and 4.43 (2t, 2H, J=7.2 Hz); 2.35 (t, 2H, J=7.5 Hz); 1.95 (m, 2H); 1.63 (m, 2H); 1.26 (m, 14H). FABMS: m/z 269 (M+H); 251 and 241. HRMS: m/z=C13H24N4O2Li, calc: 275.2059, found: 275.2004 (M+Li).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 1 h and at 55° C. for 1.5 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue was treated with 1N HCl(5 ml)
  4. extractionextracted with EtOAc (2×10 ml)
  5. washThe organic layer was washed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was crystallized from EtOAc/Hexane

Sources & evidence

ORD record
ord-a0ff9ad5747c47d88ccfb50adf225ad1
Source dataset
uspto-grants-1995_03
Patent number
US05397701

Reaction notes

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