Ethylmorpholine → HCID 54292613, compound

HRID 1448743Notes

Reaction equation

HRID 1448743 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(OCC(C)C)=O.C(N1CCOCC1)C.[CH2:35]([NH2:40])[CH2:36][CH2:37][CH2:38][CH3:39]>O1CCCC1>[CH2:35]([NH:40][C:13](=[O:15])[C@@H:12]1[CH2:16][CH2:17][CH2:18][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH2:36][CH2:37][CH2:38][CH3:39]

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 8060PentylamineHCID 62365Isobutyl chloroformateHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 54292613HCID 54292613, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

12.46 g (0.05 mol) of N-benzyloxycarbonyl-L-proline were dissolved in 100 ml of dry tetrahydrofuran and the solution was cooled to -10° C. The solution was stirred and there were added thereto 6.56 ml (0.05 mol) of isobutyl chloroformate and 6.35 ml (0.05 mol) of N-ethylmorpholine. The mixture was then stirred at -10° C. for 15 minutes. 5.76 ml (0.05 mol) of n-pentylamine were then added and the resulting mixture was stirred at 0° C. for 1 hour and then at room temperature for 16 hours. The mixture was evaporated to an oil and 400 ml of water were added. The resulting mixture was extracted with two 150 ml portions of ethyl acetate, the organic layers were combined and washed successively with two 100 ml portions of 5% citric acid solution, once with 100 ml of water, twice with 100 ml portions of 5% sodium bicarbonate solution and once with 100 ml of water. The organic layer was dried over sodium sulphate, evaporated to an oil and triturated with 350 ml of petroleum ether. On scratching, the product crystallized out, was filtered off and washed with 100 ml of petroleum ether. There were thus obtained 10.16 g (64%) of N-benzyloxycarbonyl-L-proline n-pentylamide of melting point 74°-76° C. A second crop (0.800 g) of melting point 76°-79° C. was obtained from the mother liquor.

Workup

  1. additionthere were added
  2. stirringThe mixture was then stirred at -10° C. for 15 minutes
  3. stirringthe resulting mixture was stirred at 0° C. for 1 hour
  4. customThe mixture was evaporated to an oil and 400 ml of water
  5. additionwere added
  6. extractionThe resulting mixture was extracted with two 150 ml portions of ethyl acetate
  7. washwashed successively with two 100 ml portions of 5% citric acid solution, once with 100 ml of water, twice with 100 ml portions of 5% sodium bicarbonate solution and once with 100 ml of water
  8. dry with materialThe organic layer was dried over sodium sulphate
  9. customevaporated to an oil
  10. customtriturated with 350 ml of petroleum ether
  11. customthe product crystallized out
  12. filtrationwas filtered off
  13. washwashed with 100 ml of petroleum ether
  14. customA second crop (0.800 g) of melting point 76°-79° C. was obtained from the mother liquor

Sources & evidence

ORD record
ord-5417ac57f34043609d530438626b5315
Source dataset
uspto-grants-1980_02
Patent number
US04187216

Reaction notes

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