Ethylmorpholine → HCID 18108659, compound

HRID 1448726Notes

Reaction equation

HRID 1448726 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([OH:16])=O)[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.[CH:33]1([NH2:39])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>O1CCCC1.CN(C)C=O>[CH:33]1([NH:39][C:14](=[O:16])[C@H:12]([CH3:13])[NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 7965CyclohexylamineHCID 62365Isobutyl chloroformateHCID 736104N-carbobenzyloxyalanine

Product 1

HCID 18108659HCID 18108659, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

11.15 g (0.05 mol) of N-benzyloxycarbonyl-L-alanine were dissolved in 75 ml of dry tetrahydrofuran and the mixture was cooled to -10° C. 6.35 ml (0.05 mol) of N-ethylmorpholine were added followed by 6.5 ml of isobutyl chloroformate and the solution obtained was stirred at -10° C. for 20 minutes. A solution of 6.05 ml of cyclohexylamine in 75 ml of tetrahydrofuran was then added and the resulting solution was stirred at 0° C. After 30 minutes the mixture solidified and 30 ml of dimethylformamide were added. After stirring for a further 1 hour at 0° C., the solvent was removed by evaporation, water was added and the solid filtered off. The solid was washed with 150 ml of 1-N hydrochloric acid, 150 ml of water, 150 ml of 5% sodium bicarbonate solution and 150 ml of water and then dried in vacuo. Recrystallisation from ethyl acetate yielded 11.7 g (77%) of N-benzyloxycarbonyl-L-alanine cyclohexylamide of melting point 163°-164° C.

Workup

  1. customthe solution obtained
  2. stirringthe resulting solution was stirred at 0° C
  3. waitAfter 30 minutes the mixture solidified
  4. stirringAfter stirring for a further 1 hour at 0° C.
  5. customthe solvent was removed by evaporation, water
  6. additionwas added
  7. filtrationthe solid filtered off
  8. washThe solid was washed with 150 ml of 1-N hydrochloric acid, 150 ml of water, 150 ml of 5% sodium bicarbonate solution and 150 ml of water
  9. customdried in vacuo
  10. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-f6e9167cc433406caef2cdc7a6db82b7
Source dataset
uspto-grants-1980_02
Patent number
US04187216

Reaction notes

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