Ethyl Acetate → HCID 178427466, compound

HRID 1244896Notes

Reaction equation

HRID 1244896 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:4]([NH:16][CH2:17][CH2:18][NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[N:3]=1.[NH2:30][C@H:31]1[CH2:36][CH2:35][C@H:34]([NH2:37])[CH2:33][CH2:32]1.CCOC(C)=O>O>[ClH:1].[ClH:1].[NH2:30][C@H:31]1[CH2:36][CH2:35][C@H:34]([NH:37][C:2]2[N:10]=[C:9]3[C:5]([N:6]=[CH:7][N:8]3[CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[C:4]([NH:16][CH2:17][CH2:18][NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[N:3]=2)[CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21922989HCID 21922989, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178427466HCID 178427466, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

320 mg of the product obtained in Stage 1 above and 844 mg of trans-1,4-diaminocyclohexane are mixed together and the reaction medium is heated to approximately 140° C. for approximately 3 hours then lowered to 80° C., 5 ml AcOEt, then 10 ml of water are added warm. The reaction medium is left to return to ambient temperature, followed by extracting with 2×10 ml of ethyl acetate, washing with 10 ml of a saturated solution of sodium chloride then drying. After purification by chromatography on silica eluting with methylene chloride/methanol/ammonium hydroxide in a proportion of 90/10/1, 1.5 ml of hydrochloric acid/ethanol 1.4N, is added followed by leaving to crystallize, filtering, rinsing with 5 ml of ether and drying under vacuum. In this way 173 mg of expected product is obtained in the form of white crystals.

Workup

  1. customthen lowered to 80° C.
  2. temperaturewarm
  3. waitThe reaction medium is left
  4. customto return to ambient temperature
  5. extractionby extracting with 2×10 ml of ethyl acetate
  6. washwashing with 10 ml of a saturated solution of sodium chloride
  7. customthen drying
  8. customAfter purification by chromatography on silica eluting with methylene chloride/methanol/ammonium hydroxide in a proportion of 90/10/1, 1.5 ml of hydrochloric acid/ethanol 1.4N
  9. additionis added
  10. customby leaving
  11. customto crystallize
  12. filtrationfiltering
  13. washrinsing with 5 ml of ether
  14. customdrying under vacuum

Sources & evidence

ORD record
ord-a6bbfe52748a4daf8f3b8b525d58e9b2
Source dataset
uspto-grants-2006_10
Patent number
US07122669B1

Reaction notes

Loading…