Ethylmorpholine → HCID 14181588, compound

HRID 569854Notes

Reaction equation

HRID 569854 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH:16]1([C:21]([OH:23])=O)[CH2:20][CH2:19][CH2:18][CH2:17]1.C1(C)C(S(O)(=O)=O)=CC=CC=1.C([O:42][C:43](=[O:49])[C@H:44]([CH2:46][CH2:47][CH3:48])[NH2:45])C1C=CC=CC=1.C(N1CCOCC1)C>ClCCl.CN(C)C=O>[CH:16]1([C:21]([NH:45][C@H:44]([C:43]([OH:49])=[O:42])[CH2:46][CH2:47][CH3:48])=[O:23])[CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 18840Cyclopentanecarboxylic acidHCID 86742072HCID 86742072, compound

Product 1

HCID 14181588HCID 14181588, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A cool solution of 15 mmoles of dicyclohexylcarbodiimide in dichloromethane is added to a solution of 15 mmoles of cyclopentanecarboxylic acid in dichloromethane, at -5° C. 15 mmoles of norvaline benzyl ester toluenesulfonate salt in dimethylformamide (DMF), which is neutralized with N-ethyl morpholine, is then added. The reaction mixture is stirred at 0° C. initially and then at room temperature until the reaction is completed as judged by TLC. Dicyclohexylurea is removed by filtration and 50 ml of ethyl acetate is added to the filtrate. The organic phase is washed until neutral, dried over anhydrous MgSO4 and filtered. The solvent is removed with a rotary evaporator. The residue is crystalized from isopropanol and hexane.

Workup

  1. additionis then added
  2. customat room temperature
  3. customDicyclohexylurea is removed by filtration and 50 ml of ethyl acetate
  4. additionis added to the filtrate
  5. washThe organic phase is washed until neutral,
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customThe solvent is removed with a rotary evaporator
  9. customThe residue is crystalized from isopropanol and hexane

Sources & evidence

ORD record
ord-b53a188d7d65495780b86e4d39c18034
Source dataset
uspto-grants-1988_03
Patent number
US04734420

Reaction notes

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