Ethylmorpholine → HCID 21344944, compound

HRID 2185663Notes

Reaction equation

HRID 2185663 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:20][CH3:21])[C:10]([N:12]1[CH2:19][CH2:18][CH2:17][C@H:13]1[C:14]([OH:16])=O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC(C)C)=O.C(N1CCOCC1)C.[CH2:38]([NH2:41])[CH2:39][CH3:40]>O1CCCC1.C(OCC)(=O)C>[CH2:38]([NH:41][C:14](=[O:16])[C@@H:13]1[CH2:17][CH2:18][CH2:19][N:12]1[C:10](=[O:11])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:20][CH3:21])[CH2:39][CH3:40]

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 7852PropylamineHCID 62365Isobutyl chloroformateHCID 11044788HCID 11044788, compound

Product 1

HCID 21344944HCID 21344944, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-10 °C

Procedure

2 g of 1-(N-(tert-butoxycarbonyl)-2(S)-amino-butyryl)-L-proline (6.6 mmol) prepared as in Example 2 c) are dissolved in tetrahydrofuran (40 ml). 0.86 ml of isobutyl chloroformate (6.6 mmol) and 0.85 ml of N.-ethylmorpholine (6.6 mmol) are then added to this solution, at −10° C. and under nitrogen. After stirring at −10° C. for 20 minutes, 2.75 ml of n-propylamine (33.0 mmol) are added. The mixture is left stirring at 0° C. for one hour and then at room temperature overnight. The solvent is evaporated off under vacuum and a white semi-solid material is obtained. It is dissolved in ethyl acetate (150 ml) and washed with 5% citric acid (30 ml), saturated sodium bicarbonate solution (30 ml) and brine (20 ml). After drying (Na2SO4) the mixture is filtered and the solvent is evaporated off. An oil is obtained, which is purified by liquid chromatography on a column (eluent: ethyl acetate) and a white solid is obtained.

Workup

  1. waitThe mixture is left
  2. stirringstirring at 0° C. for one hour
  3. customat room temperature
  4. customovernight
  5. customThe solvent is evaporated off under vacuum
  6. customa white semi-solid material is obtained
  7. washwashed with 5% citric acid (30 ml), saturated sodium bicarbonate solution (30 ml) and brine (20 ml)
  8. dry with materialAfter drying (Na2SO4) the mixture
  9. filtrationis filtered
  10. customthe solvent is evaporated off
  11. customAn oil is obtained
  12. customwhich is purified by liquid chromatography on a column (eluent: ethyl acetate)
  13. customa white solid is obtained

Sources & evidence

ORD record
ord-5e168d2d0d804b3ab18cfe3dc6c8039e
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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