Chloroform → HCID 178514623, compound

HRID 353919Notes

Reaction equation

HRID 353919 reaction equation
[C:1]1([CH2:11][C:12]([NH:14][C:15]2[N:16]=[CH:17][N:18]([C@H:20]3[CH2:23][C@H:22](OS(C4C=CC(C)=CC=4)(=O)=O)[CH2:21]3)[CH:19]=2)=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[N-:35]=[N+:36]=[N-:37].[Na+].C(Cl)(Cl)Cl>C(O)C.O>[N:35]([C@@H:22]1[CH2:23][C@H:20]([N:18]2[CH:19]=[C:15]([NH:14][C:12](=[O:13])[CH2:11][C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)[N:16]=[CH:17]2)[CH2:21]1)=[N+:36]=[N-:37]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 33557Sodium AzideHCID 178427790HCID 178427790, compound

Product 1

HCID 178514623HCID 178514623, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

trans-Toluene-4-sulfonic acid 3-[4-(2-naphthalen-i -yl-acetylamino)-imidazol-1-yl]-cyclobutyl ester (Preparation 4, Step 3; 593 mg, 1.25 mmol) was mixed with sodium azide (813 mg, 12.5 mmol) in ethanol (15 mL), water (5 mL), and chloroform (5 mL). The mixture was then heated at reflux with stirring for 96 h. The solvent was removed in vacuo and the residue was diluted with water and was extracted with methylene chloride. The organic layer was dried (MgSO4), filtered, and was concentrated in vacuo. Purification by silica gel chromatography (50:1 chloroform-methanol) afforded 340 mg (79% yield) of N-[1-(cis-3-azido-cyclobutyl)-1H-imidazol-4-yl]-2-naphthalen-1-yl-acetamide; 1H NMR (400 MHz, CDCl3) δ8.41 (s, 1H), 7.98 (d, J=6.4 Hz, 1H), 7.87 (m, 1H), 7.82 (m, 1H), 7.5 (m, 2H), 7.45 (m, 3H), 7.08 (d, J=1.7 Hz, 1H), 4.2 (m, 3H), 3.75 (m, 1H), 2.85 (m, 2H), 2.35 (m, 2H); MS (AP/Cl): 347.2 (M+H)+.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux
  3. customThe solvent was removed in vacuo
  4. additionthe residue was diluted with water
  5. extractionwas extracted with methylene chloride
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationwas concentrated in vacuo
  9. customPurification by silica gel chromatography (50:1 chloroform-methanol)

Sources & evidence

ORD record
ord-858c3a2e85a348cd9d53b0d0424dcf30
Source dataset
uspto-grants-2004_06
Patent number
US06756385B2

Reaction notes

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