Ethanolamine → HCID 178516325, compound

HRID 1284986Notes

Reaction equation

HRID 1284986 reaction equation
[NH:1]1[C@H:4]([C:5]([NH:7][C@H:8]([C:15](N2CCC[C@H]2C(O)=O)=[O:16])[CH2:9][C:10]2[N:14]=[CH:13][NH:12][CH:11]=2)=[O:6])[CH2:3][C:2]1=[O:25].[CH:26]1[CH:27]=[CH:28][C:29]2[N:34](O)N=[N:32][C:30]=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[CH2:51]([CH2:53]N)[OH:52].CN(C=[O:59])C>C(Cl)(Cl)Cl.CO>[NH:1]1[C@H:4]([C:5]([NH:7][C@H:8]([C:15]([N:34]2[CH2:26][CH2:27][CH2:28][C@H:29]2[C:30]([NH:32][CH2:53][CH2:51][OH:52])=[O:59])=[O:16])[CH2:9][C:10]2[N:14]=[CH:13][NH:12][CH:11]=2)=[O:6])[CH2:3][C:2]1=[O:25]

Participants

7

Reactant 5

HCID 700EthanolamineHCID 6228Dimethylformamide2×HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 178516327HCID 178516327, compound

Product 1

HCID 178516325HCID 178516325, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

In 8 ml of DMF was dissolved 277 mg of compound (13) and then 168 mg of HOBT and 330 mg of DCC were added to the solution under ice-cooling. After maintaining a reaction for one hour under ice-cooling, the reaction was further maintained for 2 hours at room temperature. After ice-cooling again the reaction mixture, 2 ml of a DMF solution of 80 mg of monoethanolamine to maintain the reaction for one hour and thereafter, the reaction was further maintained overnight at room temperature. The precipitates were filtered off, the filtrate was concentrated to dryness, and the residue thus formed was dissolved in 10 ml of chloroform-methanol-aqueous ammonia (40:10:1) and subjected to silica gel column chromatography. Then, the product was eluted with the same solvent as above to provide 106 mg of Nα -[(S)-2-azetidinone-4-carbonyl]-L-histidyl-N-(2-hydroxyethyl)-L-prolinamide (14).

Workup

  1. temperaturecooling
  2. temperatureAfter maintaining
  3. customa reaction for one hour under ice-
  4. temperaturecooling
  5. temperatureto maintain
  6. customthe reaction for one hour
  7. temperaturethe reaction was further maintained overnight at room temperature
  8. filtrationThe precipitates were filtered off
  9. concentrationthe filtrate was concentrated to dryness
  10. customthe residue thus formed
  11. washThen, the product was eluted with the same solvent as above

Sources & evidence

ORD record
ord-9f2306b0112b426e835c5eb56b2d6818
Source dataset
uspto-grants-1986_01
Patent number
US04564609

Reaction notes

Loading…