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1-(1-tert-butylcarbonylmethyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea → 3-[3-(1-tert-butylcarbonylmethyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)ureido]benzoic acid

HRID 1979323
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1979323
[C:1]([C:5]([CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][CH:10]([NH:25][C:26]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([O:37]CC3C=CC=CC=3)=[O:36])[CH:30]=2)=[O:27])[C:9]1=[O:45])=[O:6])([CH3:4])([CH3:3])[CH3:2]>[C].[Pd].CO>[C:1]([C:5]([CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][CH:10]([NH:25][C:26](=[O:27])[NH:28][C:29]2[CH:30]=[C:31]([CH:32]=[CH:33][CH:34]=2)[C:35]([OH:37])=[O:36])[C:9]1=[O:45])=[O:6])([CH3:4])([CH3:2])[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 212019451-(1-tert-butylcarbonylmethyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea

Produkt 1

HCID 227094293-[3-(1-tert-butylcarbonylmethyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)ureido]benzoic acidAusbeute 26,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 887
Methanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Methanol (20 ml) and 10% palladium carbon (68 mg) were added to 1-(1-tert-butylcarbonylmethyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(3-benzyloxycarbonylphenyl)urea (635 mg), the mixture was stirred at 50° C. under hydrogen atmosphere for 2 hours. The reaction mixture was filtrated, the filtrate was concentrated under reduced pressure. The residue was dissolved in 2 N aqueous sodium hydroxide, washed with ether, adjusted to pH 2 with concentrated hydrochloric acid, and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under the pressure, the mixed solvent of isopropyl ether and ethyl acetate was added to the residue for trituration, and collected by filtration, to thereby obtain 144 mg of the title compound as a colorless solid.

Aufarbeitung

  1. filtrationThe reaction mixture was filtrated
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 2 N aqueous sodium hydroxide
  4. washwashed with ether
  5. extractionextracted with chloroform
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under the pressure
  8. additionthe mixed solvent of isopropyl ether and ethyl acetate was added to the residue for trituration
  9. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-0b3fab76ae5c4f998aee75f779509ca8
Quelldatensatz
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06239131B1

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