Triethylamine → HCID 22241627, compound

HRID 892011Notes

Reaction equation

HRID 892011 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18](=[O:20])[CH3:19])[N:13]=[C:12]2[CH2:21][CH:22](O)[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(Cl)(=O)=O.C(N(CC)CC)C.[NH4+].[Cl-].[N-:39]=[N+:40]=[N-:41].[Na+]>C(Cl)Cl.CCOCC.O.C(OCC)(=O)C>[N:39]([CH:22]([CH3:23])[CH2:21][C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=2)[N:14]([C:18](=[O:20])[CH3:19])[N:13]=1)=[N+:40]=[N-:41]

Participants

10

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 22241626HCID 22241626, compound

Product 1

HCID 22241627HCID 22241627, compoundYield 92.8%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the product from Step B (0.12 g, 0.37 mmol) and methanesulfonyl chloride (0.04 ml, 0.48 mmol) in CH2Cl2 (5 ml) and under nitrogen was cooled to 0° C. and triethylamine (0.07 ml, 0.48 mmol) was added. The resulting mixture was stirred at 0° C. for 10 min followed by the addition of a saturated aqueous solution of NH4Cl (20 ml) and ethyl acetate (20 ml). The aqueous layer was separated and extracted with ethyl acetate (2×5 ml). The combined extracts were washed with a saturated aqueous solution of NaCl (2×15 ml), dried (MgSO4), and evaporated to a residue which was dissolved in DMF (3 ml). Sodium azide (0.08 g, 1.2 mmol) was added and the mixture was stirred at 70° C. for 18 h. After cooling, water (20 ml) and ether (20 ml) were added and the aqueous layer was separated and further extracted with ether (3×20 ml). The combined extracts were washed with a saturated aqueous solution of NaCl (3×15 ml), dried (MgSO4), and evaporated to a residue that was purified by chromatography (silica, 10% ethyl acetate in hexane) to give a yellow oil (0.12 g). MS(ES) m/z 350 (M+H)+.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (2×5 ml)
  3. washThe combined extracts were washed with a saturated aqueous solution of NaCl (2×15 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated to a residue which
  6. dissolutionwas dissolved in DMF (3 ml)
  7. stirringthe mixture was stirred at 70° C. for 18 h
  8. temperatureAfter cooling
  9. customthe aqueous layer was separated
  10. extractionfurther extracted with ether (3×20 ml)
  11. washThe combined extracts were washed with a saturated aqueous solution of NaCl (3×15 ml)
  12. dry with materialdried (MgSO4)
  13. customevaporated to a residue that
  14. customwas purified by chromatography (silica, 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-47855e3af4964d2795ef7e6b9611e6f0
Source dataset
uspto-grants-2006_02
Patent number
US07005443B1

Reaction notes

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