Hydrochloric Acid → HCID 23001302, compound

HRID 398012Notes

Reaction equation

HRID 398012 reaction equation
[Si:1]([O:18][C:19]1[CH:20]=[C:21]([C:25]#[C:26][CH2:27][CH2:28]O)[CH:22]=[CH:23][CH:24]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P([N:44]=[N+:45]=[N-:46])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1.Cl.[N-]=[N+]=[N-].[Na+].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.CN(C=O)C>[N:44]([CH2:28][CH2:27][C:26]#[C:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[N+:45]=[N-:46]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 70026670HCID 70026670, compound

Product 1

HCID 23001302HCID 23001302, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of alcohol from Step B (375 mg, 0.936 mmol) and diphenylphosphoryl azide (0.242 mL, 1.12 mmol) in toluene (3 mL) at 0° C. was added DBU (0.154 mL, 1.03 mmol). The reaction mixture was stirred at 25° C. for 16 hours, then poured onto 10% HCl (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to provide a brown oil. A solution of the oil and sodium azide (66.9 mg, 1.03 mmol) in DMF (3 mL) was heated to 85° C. for 16 hours. The reaction mixture was poured onto saturated sodium bicarbonate (50 mL) and extracted with methylene chloride (3×50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by column chromatography (0→20% ethyl acetate/hexane) to provide the title compound.

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide a brown oil
  6. extractionextracted with methylene chloride (3×50 mL)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by column chromatography (0→20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1a9d498a9c0e4f4bb9183086b1a92705
Source dataset
uspto-grants-2003_08
Patent number
US06610722B2

Reaction notes

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