Dicyclohexylcarbodiimide → HCID 54545224, compound

HRID 266360Notes

Reaction equation

HRID 266360 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([CH2:16][CH2:17][CH2:18][CH3:19])[C:13]([OH:15])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:23][CH:22]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C@@H:12]([CH2:16][CH2:17][CH2:18][CH3:19])[C:13]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:25][CH:26]=2)=[O:15])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 225219p-Aminophenylacetic acid ethyl esterHCID 33699753HCID 33699753, compound

Product 1

HCID 54545224HCID 54545224, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-(4-chlorobenzenesulfonylamino)hexanoic acid (3 g) and ethyl 4-aminophenylacetate (2.116 g) were dissolved in dichloromethane (50 ml). To the solution, N,N'-dicyclohexylcarbodiimide (2.43 g) was added, and then the whole was stirred at room temperature overnight under argon. The reaction mixture was concentrated, poured in a saturated saline solution and extracted with ethyl acetate. The combined ethyl acetate layers were washed with a saturated saline solution and dried over Na2SO4. The solvent was evaporated under reduced pressure, and the resulting crude product was recrystallized from ethanol to obtain (S)-2-(4-chlorobenzenesulfonylamino)-N-(4-(ethoxycarbonylmethyl)phenyl)hexanamide (1.493 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionpoured in a saturated saline solution
  3. extractionextracted with ethyl acetate
  4. washThe combined ethyl acetate layers were washed with a saturated saline solution
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-62cfe45ac5aa4eeba2e97afa9ce02d4e
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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