Ethylmorpholine → HCID 53667817, compound

HRID 1448742Notes

Reaction equation

HRID 1448742 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([N:16]1[CH2:23][CH2:22][CH2:21][C@H:17]1[C:18]([OH:20])=O)=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1CCOCC1)C.ClC(OCC(C)C)=O.[CH2:40]([NH2:45])[CH2:41][CH2:42][CH2:43][CH3:44]>O1CCCC1>[CH2:40]([NH:45][C:18](=[O:20])[C@@H:17]1[CH2:21][CH2:22][CH2:23][N:16]1[C:14](=[O:15])[C@H:12]([CH3:13])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH2:41][CH2:42][CH2:43][CH3:44]

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 8060PentylamineHCID 62365Isobutyl chloroformateHCID 5388928Z-Ala Prolinal

Product 1

HCID 53667817HCID 53667817, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

2 g (0.06 mol) of N-benzyloxycarbonyl-L-alanyl-L-proline were dissolved in 20 ml of dry tetrahydrofuran and the solution was cooled to -10° C. 0.76 ml (0.06 mol) of N-ethylmorpholine and 0.79 ml (0.006 mol) of isobutyl chloroformate were added and the resulting mixture was stirred at -10° C. for 20 minutes. 0.69 ml (0.006 mol) of n-pentylamine was then added and the resulting solution was stirred at -20° C. for 1 hour and then left to stand at room temperature overnight. The solution was then evaporated to an oil which was dissolved in ethyl acetate. The ethyl acetate solution was washed twice with water, twice with 5% citric acid solution, once with water, twice with 5% sodium bicarbonate solution and twice with water, dried and evaporated to an oil. The desired N-benzyloxycarbonyl-L-alanyl-L-proline n-pentylamide was crystallised from ethyl acetate/petroleum ether in a yield of 1 g (42.8%) and with a melting point of 102°-104° C.

Workup

  1. stirringthe resulting solution was stirred at -20° C. for 1 hour
  2. waitleft
  3. waitto stand at room temperature overnight
  4. customThe solution was then evaporated to an oil which
  5. dissolutionwas dissolved in ethyl acetate
  6. washThe ethyl acetate solution was washed twice with water, twice with 5% citric acid solution, once with water, twice with 5% sodium bicarbonate solution and twice with water
  7. customdried
  8. customevaporated to an oil
  9. customThe desired N-benzyloxycarbonyl-L-alanyl-L-proline n-pentylamide was crystallised from ethyl acetate/petroleum ether in a yield of 1 g (42.8%) and with a melting point of 102°-104° C.

Sources & evidence

ORD record
ord-38d44c2166d345b7b08f7956245d1798
Source dataset
uspto-grants-1980_02
Patent number
US04187216

Reaction notes

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