HCID 59049327, compound → HCID 59049307, compound

HRID 1264483Notes

Reaction equation

HRID 1264483 reaction equation
C(OC([N:11]1[CH2:14][CH2:13][C@H:12]1[C:15]1[N:19]([CH2:20][CH2:21][CH2:22][C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[N:18]=[N:17][N:16]=1)=O)C1C=CC=CC=1>C(O)C.[Pd]>[N:25]1[CH:26]=[CH:27][CH:28]=[C:23]([CH2:22][CH2:21][CH2:20][N:19]2[C:15]([C@@H:12]3[CH2:13][CH2:14][NH:11]3)=[N:16][N:17]=[N:18]2)[CH:24]=1

Participants

4

Reactant 1

HCID 59049327HCID 59049327, compound

Product 1

HCID 59049307HCID 59049307, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(2S)-1-(Benzyloxycarbonyl)-2-(1-[3-(3-pyridyl)-1-propyl]-1H-tetrazol-5-yl)azetidine from Reference Example 17 (125.3 mg, 0.331 mmol, 1.0 eq) was dissolved in ethanol (20 mL) and 10% Pd/C (49.9 mg, 0.047 mmol, 0.14 eq) was carefully added. The mixture was flushed with vacuum and nitrogen three times and stirred under a hydrogen atmosphere at about room temperature for about 26 hours. After removing the solid matter by filtration, the solvent was removed under vacuum to give 80.8 mg (quantitative yield) of the product as a colorless oil. 1H NMR (CDCl3) δ 2.18-3.24 (series of m, 7H); 3.46-4.68 (series of m, 5H); 7.19-7.33 (m, 1H); 7.51-7.63 (m, 1H); 8.38-8.57 (m, 2H).

Workup

  1. customThe mixture was flushed with vacuum and nitrogen three times
  2. customAfter removing the solid matter
  3. filtrationby filtration
  4. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-019a7228a3f648b8b893780e04b9c643
Source dataset
uspto-grants-2003_04
Patent number
US06544976B1

Reaction notes

Loading…