Ethylmorpholine → HCID 14181528, compound

HRID 2309034Notes

Reaction equation

HRID 2309034 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH:16]1([C:21]([OH:23])=O)[CH2:20][CH2:19][CH2:18][CH2:17]1.C([O:31][C:32](=[O:42])[C@H:33]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[NH2:34])C1C=CC=CC=1.C(N1CCOCC1)C>ClCCl.CN(C=O)C>[CH:16]1([C:21]([NH:34][C@H:33]([C:32]([OH:42])=[O:31])[CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:23])[CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 18840Cyclopentanecarboxylic acidHCID 736312Benzyl 3-phenyl-L-alaninate

Product 1

HCID 14181528HCID 14181528, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A cool solution of 2.06 gm of dicyclohexylcarbodiimide in 10 ml of dichloromethane was added to a solution of 1.4114 gm of cyclopentanecarboxylic acid in 5 ml of dichloromethane at -5° C. It was followed by the addition of 4.28 gm of phenylalanine benzyl ester touluenesulfonate salt in 10 ml of DMF which was neutralized with 1.36 ml of N-ethyl morpholine. The reaction mixture was stirred at 0° C. for one hour and then at room temperature for three hours. Dicyclohexylurea was removed by filtration and 50 ml of ethyl acetate was added to the filtrate. The organic phase was washed until neutral, dried over anhydrous MgSO4 and filtered. The solvent was removed with a rotary evaporator. The residue was crystallized from isopropanol and hexane yielding 2.35 gm of white crystals having a melting point of 88°-89° C. Elemental analysis of these crystals yielded the following.

Workup

  1. waitat room temperature for three hours
  2. customDicyclohexylurea was removed by filtration and 50 ml of ethyl acetate
  3. additionwas added to the filtrate
  4. washThe organic phase was washed until neutral,
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed with a rotary evaporator
  8. customThe residue was crystallized from isopropanol and hexane yielding 2.35 gm of white crystals
  9. customElemental analysis of these crystals yielded the following

Sources & evidence

ORD record
ord-ad273bef0e71432c9a91ed13fc17754d
Source dataset
uspto-grants-1987_09
Patent number
US04692458

Reaction notes

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