p-Toluenesulfonic acid → HCID 19032873, Verbindung

HRID 266275

Reaktionsgleichung

Reaktionsgleichung von HRID 266275
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:18]([O:25][C:26]([NH:28][CH:29]([C:32]([OH:34])=O)[CH2:30][OH:31])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.[NH2:36][C:37]1[CH:42]=[CH:41][C:40]([CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])=[CH:39][CH:38]=1.[I-].ClC1C=CC=C[N+]=1C>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:18]([O:25][C:26]([NH:28][CH:29]([CH2:30][O:31][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1)[C:32]([NH:36][C:37]1[CH:38]=[CH:39][C:40]([CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])=[CH:41][CH:42]=1)=[O:34])=[O:27])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

8

Edukt 5

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 76007N-carbobenzoxy-serineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 24192282Ethyl (4-aminophenyl)acetate--hydrogen chloride (1/1)

Produkt 1

HCID 19032873HCID 19032873, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Dihydropyran (2.27 ml) and p-toluenesulfonic acid (500 mg) were added to a suspension of N-benzyloxycarbonyl-DL-serine (5 g) in chloroform, and the mixture was stirred at room temperature overnight under argon. Triethylamine (11.65 ml), ethyl p-aminophenylacetate hydrochloride (4.5 g) and 2-chloro-1-methylpyridinium iodide (6.4 g) were added to the reaction mixture and the whole was refluxed for 3 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with 1N HCl, 5% NaHCO3, and saturated saline solution, and dried over Na2SO4. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel=300 g, hexane/ethyl acetate=20/9) to obtain (RS)-2-(benzyloxycarbonylamino)-N-(4-(ethoxycarbonylmethyl)phenyl)-3-(tetrahydropyran-2-yloxy)propanamide (6.847 g).

Aufarbeitung

  1. temperaturethe whole was refluxed for 3 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with 1N HCl, 5% NaHCO3, and saturated saline solution
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel=300 g, hexane/ethyl acetate=20/9)

Quellen und Nachweise

ORD-Eintrag
ord-0d5c982a28654fc2b499ed220543d88c
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05650428

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