Triethylamine → HCID 22285722, compound

HRID 1061728Notes

Reaction equation

HRID 1061728 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[CH2:24][CH2:23][CH2:22][C:13]3=[N:14][N:15]([CH2:18][CH:19](O)[CH3:20])[C:16]([CH:17]=1)=[C:12]23)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:37]=[N+:38]=[N-:39].[Na+]>ClCCl.O>[N:37]([CH:19]([CH3:20])[CH2:18][N:15]1[C:16]2[CH:17]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=[C:11]3[CH2:24][CH2:23][CH2:22][C:13]([C:12]=23)=[N:14]1)=[N+:38]=[N-:39]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 22285729HCID 22285729, compound

Product 1

HCID 22285722HCID 22285722, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
70 °C

Procedure

To a stirred solution of the product from Step F (0.77 g, 2.4 mmol) in dichloromethane (10 mL) was added triethylamine (0.40 mL, 2.9 mmol) followed by methanesulfonyl chloride (0.22 mL, 2.9 mmol) at 0° C. After 30 min, dichloromethane (50 mL) was added followed by water (50 mL). The organic layer was separated and the aqueous was extracted with dichloromethane (2×50 mL). The combined extracts were washed with brine (30 mL), dried (MgSO4), and evaporated to a residue that was taken up in DMF (6 mL) and sodium azide (0.33 g, 5.0 mmol) was added. The reaction mixture was heated at 70° C. for 17 h, poured into water, and extracted with ether (3×50 mL). The combined extracts were washed with brine, dried (MgSO4), and evaporated to a residue that was purified by column chromatography (silica, hexane to 10% ethyl acetate in hexane) to give an oil (0.75 g, 90%): MS (ES) m/z 348 (M+).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous was extracted with dichloromethane (2×50 mL)
  3. washThe combined extracts were washed with brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated to a residue that
  6. extractionextracted with ether (3×50 mL)
  7. washThe combined extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated to a residue that
  10. customwas purified by column chromatography (silica, hexane to 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b59b3c27591b4713b709284f3b22c32c
Source dataset
uspto-grants-2005_11
Patent number
US06960608B2

Reaction notes

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