Hydrochloric Acid → (4-Morpholinecarbonylphenylalanyl)-2-phenethyl-1-phenylsulfonyl ethylenediamine

HRID 378330Notes

Reaction equation

HRID 378330 reaction equation
[N:1]1([C:7]([C:9]2[CH:20]=[CH:19][C:12]([CH2:13][C@@H:14]([C:16]([OH:18])=O)[NH2:15])=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.N[C@H:22]([C:30](O)=O)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C[N:34]1CCOCC1.ClC(OCC(C)C)=O.Cl.C(C(N)[CH:58]([S:60]([C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)(=[O:62])=[O:61])[NH2:59])CC1C=CC=CC=1.C1(S(N[C@H](C(O)=O)CCC2C=CC=CC=2)(=O)=O)C=CC=CC=1.N.C1COCC1.C(=[N-])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1.O1CCOCC1.C(Cl)Cl>[N:1]1([C:7]([C:9]2[CH:10]=[CH:11][C:12]([CH2:13][C@@H:14]([C:16]([NH:34][CH:30]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:58]([S:60]([C:63]3[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=3)(=[O:62])=[O:61])[NH2:59])=[O:18])[NH2:15])=[CH:19][CH:20]=2)=[O:8])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

14

Reactant 10

HCID 313Hydrochloric AcidHCID 6140L-PhenylalanineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 105034IsocyanateHCID 193530722-Phenethyl-1-phenylsulfonylethylenediamine hydrochlorideHCID 21226445Aluminium lithium hydrideHCID 21967295HCID 21967295, compoundHCID 21982362Ammonia tetrahydrofuranHCID 573014314-Morpholinecarbonylphenylalanine

Product 1

HCID 131721709(4-Morpholinecarbonylphenylalanyl)-2-phenethyl-1-phenylsulfonyl ethylenediamineYield 89%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-morpholinecarbonylphenylalanine (Mu-PheOH, 0.14 g, 0.48 mmol, prepared according to the method described in Esser, R. et.al., Arthritis & Rheumatism (1994), 37, 236) in THF (10 mL)) at -10° C. were added 4-methylmorpholine (0.11 mL, 0.96 mmol), followed by isobutyl chloroformate (64 μL, 0.48 mmol). After 5 minute activation, 2-phenethyl-1-phenylsulfonylethylenediamine hydrochloride (0.15 g, 0.44 mmol, prepared by conversion of the N-phenylsulfonylhomophenylalanine to the amide via CDl/NH3 /THF reaction, then by reduction of the carbonyl amide to its corresponding amine with lithium aluminium hydride, followed by treatment with HCl in dioxane) was added. After 1 hour, the reaction mixture was diluted with CH2Cl2 (50 mL) and washed with 1 M HCl (50 mL) followed by saturated aqueous NaHCO3 (50 mL), dried over MgSO4, filtered, and the solvent was removed under reduced pressure. The residue was diluted with CH2Cl2 (5 mL) and precipated from hexane (200 mL), filtered, and dried in vacuo yielding 0.22 g (89%) of the desired product.

Workup

  1. additionwas added
  2. washwashed with 1 M HCl (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. additionThe residue was diluted with CH2Cl2 (5 mL)
  7. filtrationfiltered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-3b6f4b69d1804138b7ca8c20ab5bc88c
Source dataset
uspto-grants-2000_02
Patent number
US06030946

Reaction notes

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