Triethylamine → HCID 9881916, compound

HRID 394663Notes

Reaction equation

HRID 394663 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:15]=[CH:14][C:13]3[O:12][CH2:11][CH:10](C(O)=O)[CH2:9][C:8]=3[C:7]=2[CH:19]=1.[CH2:20]([N:22](CC)CC)[CH3:21].ClC(OCC)=[O:29].[N-]=[N+]=[N-].[Na+]>CC(C)=O.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:15]=[CH:14][C:13]3[O:12][CH2:11][CH:10]([NH:22][C:20](=[O:29])[CH3:21])[CH2:9][C:8]=3[C:7]=2[CH:19]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 18177441HCID 18177441, compound

Product 1

HCID 9881916HCID 9881916, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

After dissolving the acid obtained in Step B (50 mg:0.19 mmol) in acetone (2 ml) under an inert atmosphere, distilled triethylamine (0.07 ml:0.52 mmol:2.7 eq.) and also distilled ethyl chloroformate (0.06 ml:0.68 mmol:3.5 eq.) are slowly introduced in succession at 0° C. After 30 minutes of stirring, sodium azide (57 mg:0.87 mmol:4.5 eq.), dissolved in 1 ml of water, is added. After a similar amount of time has passed, the reaction medium is extracted with dichloromethane. The resulting organic phase is concentrated, taken up in 1 ml of toluene and heated at reflux for 30 minutes. While in the hot state, glacial acetic acid (1 ml) is then introduced; the heating is then continued for 1 hour 30 minutes. At ambient temperature, the products are extracted with ethyl acetate and then purified on a flash silica column CHCl3 /AcOEt 7/3. The title compound is washed with diethyl ether.

Workup

  1. additionare slowly introduced in succession at 0° C
  2. additionis added
  3. extractionthe reaction medium is extracted with dichloromethane
  4. concentrationThe resulting organic phase is concentrated
  5. temperatureheated
  6. temperatureat reflux for 30 minutes
  7. additionWhile in the hot state, glacial acetic acid (1 ml) is then introduced
  8. waitthe heating is then continued for 1 hour 30 minutes
  9. extractionAt ambient temperature, the products are extracted with ethyl acetate
  10. custompurified on a flash silica column CHCl3 /AcOEt 7/3
  11. washThe title compound is washed with diethyl ether

Sources & evidence

ORD record
ord-827070480a244d87b525f21ef7c2d680
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Reaction notes

Loading…