Ethylmorpholine → HCID 14181601, compound

HRID 1762500Notes

Reaction equation

HRID 1762500 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH:16]1([C:21](O)=[O:22])[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:50])[C:44]1([CH2:49][CH2:48][CH2:47][CH2:46]1)[NH2:45])C1C=CC=CC=1.C(N1CCOCC1)C>ClCCl.CN(C)C=O>[CH:16]1([C:21]([NH:45][C:44]2([C:43]([OH:42])=[O:50])[CH2:46][CH2:47][CH2:48][CH2:49]2)=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 18840Cyclopentanecarboxylic acidHCID 86743057HCID 86743057, compound

Product 1

HCID 14181601HCID 14181601, 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 cycloleucine 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 crystallized 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 crystallized from isopropanol and hexane

Sources & evidence

ORD record
ord-381cf7d9f3ea4835a4baaee2f5bf4bdf
Source dataset
uspto-grants-1989_05
Patent number
US04833152

Reaction notes

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