{3-(Benzyloxycarbonyl-methyl)-1-[isopropyl-(4-methoxy-phenyl)-carbamoylmethyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl}acetic acid benzyl ester → {3-(Benzyloxycarbonyl-methyl)-1-[isopropyl-(4-methoxy-phenyl)-carbamoylmethyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl}acetic acid

HRID 343104

Reaktionsgleichung

Reaktionsgleichung von HRID 343104
[CH2:1]([O:8][C:9](=[O:56])[CH2:10][C:11]1([CH2:45][C:46]([O:48]CC2C=CC=CC=2)=[O:47])[C:17](=[O:18])[N:16]([C:19]([CH:31]([CH3:33])[CH3:32])([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:20](=[O:22])[NH2:21])[C:15]2[CH:34]=[CH:35][CH:36]=[CH:37][C:14]=2[N:13]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:12]1=[O:44])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[CH2:1]([O:8][C:9]([CH2:10][C:11]1([CH2:45][C:46]([OH:48])=[O:47])[C:17](=[O:18])[N:16]([C:19]([CH:31]([CH3:33])[CH3:32])([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:20](=[O:22])[NH2:21])[C:15]2[CH:34]=[CH:35][CH:36]=[CH:37][C:14]=2[N:13]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:12]1=[O:44])=[O:56])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 86753588{3-(Benzyloxycarbonyl-methyl)-1-[isopropyl-(4-methoxy-phenyl)-carbamoylmethyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl}acetic acid benzyl ester

Produkt 1

HCID 86753587{3-(Benzyloxycarbonyl-methyl)-1-[isopropyl-(4-methoxy-phenyl)-carbamoylmethyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl}acetic acidAusbeute 32,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

450 mg (0.6 mmols) of {3-(Benzyloxycarbonyl-methyl)-1-[isopropyl-(4-methoxy-phenyl)-carbamoylmethyl]-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl}acetic acid benzyl ester, prepared as in Intermediate 27, is dissolved in 100 mL of ethyl acetate and 45 mg of 10% Pd/C is added. The reaction mixture is then kept under a hydrogen atmosphere with stirring for 2.5 h. The solution is then filtered through celite and the solvent is removed in vacuo. The resulting white solid is purified by reverse phase MPLC in methanol/water 70/30 as eluent to afford 130 mg (32%) of the title compound as a white solid: 1H NMR (CDCl3, 300 MHz) δ7.38-6.54 (m, 18H), 5.29-4.88 (m, 4H), 4.23 (m, 1H), 3.83 (d, J=7.5, 3H), 3.23-2.69 (m, 4H), 1.08-1.02 (m, 6H); low resolution MS m/e 664.

Aufarbeitung

  1. filtrationThe solution is then filtered through celite
  2. customthe solvent is removed in vacuo
  3. customThe resulting white solid is purified by reverse phase MPLC in methanol/water 70/30 as eluent

Quellen und Nachweise

ORD-Eintrag
ord-0190849fc4614cf5800ef73ea7104c43
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859007

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