Benzyl chloroformate → N-(4-{[(Benzyloxy)carbonyl]amino}-3-methylbenzoyl)threonine methyl ester

HRID 43624

Reaktionsgleichung

Reaktionsgleichung von HRID 43624
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([C@@H:18]([CH3:20])[OH:19])[NH:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[C:9]([CH3:16])[CH:8]=1.[H][H].C(=O)(O)[O-].[Na+].Cl[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]>C(O)C.[Pd].C1COCC1.O>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([C@@H:18]([CH3:20])[OH:19])[NH:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[C:9]([CH3:16])[CH:8]=1

Komponenten

9

Edukt 4

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 67548938N-(3-Methyl-4-nitrobenzoyl)threonine methyl esterHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 68406078N-(4-{[(Benzyloxy)carbonyl]amino}-3-methylbenzoyl)threonine methyl esterAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

10% Pd/C (1.2 g) was added to a solution of N-(3-methyl-4-nitrobenzoyl)threonine methyl ester obtained in Example (108a) (7.2 g, 24.3 mmol) in ethanol (40 mL), and the mixture was stirred in a hydrogen atmosphere at room temperature for one hour and 20 minutes. Pd/C was filtered off, and the filtrate was concentrated under reduced pressure. Water (20 mL), THF (20 mL), sodium bicarbonate (2.52 g, 30 mmol) and benzyl chloroformate (5.37 g, 30 mmol) were added to the resulting residue, and the mixture was stirred at room temperature for one hour. Following extraction with dichloromethane, the organic layer was washed with water, a 1 N aqueous hydrochloric acid solution and brine, dried over magnesium sulfate, and concentrated. Thereafter, the resulting residue was purified by silica gel column chromatography (elution solvent: chloroform/methanol=1/0, 95/5, 90/10, 85/15) to obtain 7.4 g of the title compound as a colorless solid (76%).

Aufarbeitung

  1. filtrationPd/C was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. extractionextraction with dichloromethane
  4. washthe organic layer was washed with water
  5. dry with materiala 1 N aqueous hydrochloric acid solution and brine, dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThereafter, the resulting residue was purified by silica gel column chromatography (elution solvent: chloroform/methanol=1/0, 95/5, 90/10, 85/15)

Quellen und Nachweise

ORD-Eintrag
ord-0bdf1f99cf0e4050beeb0918ff0f4a0d
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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