Triethylamine → HCID 58743377, compound

HRID 722825Notes

Reaction equation

HRID 722825 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C@@H:11](O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.CS(Cl)(=O)=O.[N-:40]=[N+:41]=[N-:42].[Na+]>C(Cl)Cl>[N:40]([C@H:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH3:10])=[N+:41]=[N-:42]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 58743341HCID 58743341, compound

Product 1

HCID 58743377HCID 58743377, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of alcohol 94 (48 mg, 0.12 mmol) in CH2Cl2 (1.25 mL), Et3N (52 μL, 0.37 mmol) and MsCl (24 μL, 0.31 mmol) were added. After stirring for 2 h, the mixture was quenched with H2O (10 mL), extracted with CH2Cl2 (3×10 mL), dried over Na2SO4 and concentrated in vacuo. The crude mesylate was dissolved in DMF (0.65 mL) and NaN3 (40.5 mg, 0.62 mmol) was added. The mixture was stirred at 120 C. for 3 h and then quenched with H2O (10 mL), extracted with Et2O (3×10 mL), dried over Na2SO4 and concentrated in vacuo. The crude was purified by column chromatography on silica (hexane/EtOAc 10:1 to 5:1) to obtain azide 95 as a colorless oil (25 mg, 49% yield).

Workup

  1. customthe mixture was quenched with H2O (10 mL)
  2. extractionextracted with CH2Cl2 (3×10 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude mesylate was dissolved in DMF (0.65 mL)
  6. stirringThe mixture was stirred at 120 C
  7. waitfor 3 h
  8. customquenched with H2O (10 mL)
  9. extractionextracted with Et2O (3×10 mL)
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated in vacuo
  12. customThe crude was purified by column chromatography on silica (hexane/EtOAc 10:1 to 5:1)

Sources & evidence

ORD record
ord-e96a41ac26524e5b8aaf5afd0bb80b15
Source dataset
uspto-grants-2006_11
Patent number
US07138547B2

Reaction notes

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