Hydrochloric Acid → HCID 53715534, compound

HRID 1378562Notes

Reaction equation

HRID 1378562 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=1)C(O)=O.C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:35])C=CC=CC=1.C(O)(C)(C)C.Cl>C1(C)C=CC=CC=1.O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:35])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 53634959HCID 53634959, compound

Product 1

HCID 53715534HCID 53715534, compoundYield 273.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the acid from Step 1 (8.29 g, 9.2 mmol) and triethylamine (3.46 g, 34.2 mmol) dissolved in 30 mL of anhydrous toluene, was cooled to 0° C. and treated with diphenylphosphoryl azide (8.23 g, 9.9 mmol). The solution was maintained at 0° C. for 45 minutes and warmed to room temperature for 3.75 hours. The reaction was poured into water, extracted with ether, dried over magnesium sulfate, and concentrated in vacuo to remove the ether. The remaining toluene solution was heated to 110° C. for 1 hour. Tert-Butyl alcohol (6 mL, 63 mmol) was added to the reaction mixture, after an additional twenty minutes, concentrated hydrochloric acid (2.6 mL) was cautiously added and the reaction maintained at 90° C. overnight (16 hours). After cooling the solution to room temperature, the mixture was concentrated in vacuo and the residue taken up in ethyl acetate, washed successively with water, sat. aq. NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to give a yellow solid (6.44 g, 86%): mp 54°-61° C. 1H NMR (CDCl3) 300 MHz 7.69 (d, J=7.7 Hz, 1H), 7.36 (m, 1H), 7.20-7.26 (m, 4H), 7.16 (d, J=8.5 Hz, 2H), 4.17 (s, 2H), 2.46 (s, 3H), 2.44 (s, 3H). Mass spectrum M+H=257.

Workup

  1. temperatureThe solution was maintained at 0° C. for 45 minutes
  2. temperaturewarmed to room temperature for 3.75 hours
  3. extractionextracted with ether
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto remove the ether
  7. temperatureThe remaining toluene solution was heated to 110° C. for 1 hour
  8. temperaturethe reaction maintained at 90° C. overnight (16 hours)
  9. temperatureAfter cooling the solution to room temperature
  10. concentrationthe mixture was concentrated in vacuo
  11. washwashed successively with water, sat. aq. NaHCO3 and brine
  12. dry with materialdried over anhydrous MgSO4
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c35d0424c3c453995f9fc5135a9e39d
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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