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

HRID 43631

Reaktionsgleichung

Reaktionsgleichung von HRID 43631
[CH3:1][O:2][C:3](=[O:20])[C@H:4]([CH2:18][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:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30]>C(O)C.[Pd].C1COCC1.O>[CH3:1][O:2][C:3](=[O:20])[C@H:4]([CH2:18][OH:19])[NH:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])=[C:9]([CH3:16])[CH:8]=1

Komponenten

9

Edukt 4

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 67549024N-(3-Methyl-4-nitrobenzoyl)serine methyl esterHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 67548569N-(4-{[(Benzyloxy)carbonyl]amino}-3-methylbenzoyl)serine methyl esterAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

10% Pd/C (1.2 g) was added to N-(3-methyl-4-nitrobenzoyl)serine methyl ester obtained in Example (109a) (2.39 g, 8.47 mmol) in ethanol (20 mL), and the mixture was stirred in a hydrogen atmosphere at room temperature for one hour. Pd/C was filtered off, and the filtrate was concentrated under reduced pressure. Water (10 mL), THF (10 mL), sodium bicarbonate (0.84 g, 10 mmol) and benzyl chloroformate (1.62 g, 9 mmol) were added to the resulting residue, and the mixture was stirred at room temperature for one hour. Following extraction with ethyl acetate, 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, 98/2, 96/4, 94/6, 92/8) to obtain 1.8 g of the title compound as a colorless solid (55%).

Aufarbeitung

  1. filtrationPd/C was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. extractionextraction with ethyl acetate
  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, 98/2, 96/4, 94/6, 92/8)

Quellen und Nachweise

ORD-Eintrag
ord-f5e08fe5981f4187a80d25e6047d695e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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