4-Methylmorpholine → N-[[1,2,3,4-Tetrahydro-2-[(acetylthio)methyl]-2-naphthalenyl]carbonyl]-isoserine, benzyl ester

HRID 1656056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1656056
[C:1]([C:4]1([CH2:14][S:15][C:16](=[O:18])[CH3:17])[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)([OH:3])=O.CN1CCOCC1.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH2:37]([O:44][C:45](=[O:50])[CH:46]([OH:49])[CH2:47][NH2:48])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[C:16]([S:15][CH2:14][C:4]1([C:1]([NH:48][CH2:47][CH:46]([C:45]([O:44][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:50])[OH:49])=[O:3])[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)(=[O:18])[CH3:17]

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 197899352-Carboxy-2-[(acetylthio)methyl]-1,2,3,4-tetrahydronaphthaleneHCID 88125266Isoserine benzyl ester tosylate salt

Produkt 1

HCID 88127936N-[[1,2,3,4-Tetrahydro-2-[(acetylthio)methyl]-2-naphthalenyl]carbonyl]-isoserine, benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Dissolve 2-carboxy-2-[(acetylthio)methyl]-1,2,3,4-tetrahydronaphthalene (2.88 g, 10.0 mmol) in dry dimethylformamide (20 mL). To this solution add N-methyl morpholine (1.01 g, 10.0 mmol), isoserine benzyl ester tosylate salt (3.67 g, 10.0 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.92 g, 10.0 mmol). Stir the reaction mixture for 18 hours under an atmosphere of argon at ambient temperature then partition between ethyl acetate and dilute HCl. Wash the organic solution with water, saturated sodium hydrogen carbonate then brine. Dry the solution (MgSO4) and concentrate in vacuo. Purify the residue by column chromatography (ethyl acetate:hexane) to give the title compound.

Aufarbeitung

  1. customthen partition between ethyl acetate and dilute HCl
  2. washWash the organic solution with water, saturated sodium hydrogen carbonate
  3. dry with materialDry the solution (MgSO4)
  4. concentrationconcentrate in vacuo
  5. customPurify the residue by column chromatography (ethyl acetate:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-abd1491b6eac43038c4de47262fb2b6e
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05252601

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