4-(2,3-dihydro-1,3-dioxo-1H-pyrrolo[3,4-c]pyridin-2-yl)-N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine → N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-4-[(3aRS, 7aRS)-(octahydro-1,3-dioxo-1H-pyrrolo[3,4-c]pyridin-2-yl)]-L-phenylalanine

HRID 393438

Reaktionsgleichung

Reaktionsgleichung von HRID 393438
[O:1]=[C:2]1[C:10]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[C:4](=[O:11])[N:3]1[C:12]1[CH:39]=[CH:38][C:15]([CH2:16][C@@H:17]([C:35]([OH:37])=[O:36])[NH:18][C:19]([C:21]2([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])=[CH:14][CH:13]=1>C(O)C.C(O)(C(F)(F)F)=O>[CH3:34][O:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][C:21]2([C:19]([NH:18][C@H:17]([C:35]([OH:37])=[O:36])[CH2:16][C:15]3[CH:38]=[CH:39][C:12]([N:3]4[C:2](=[O:1])[CH:10]5[CH:5]([CH2:6][NH:7][CH2:8][CH2:9]5)[C:4]4=[O:11])=[CH:13][CH:14]=3)=[O:20])[CH2:22][CH2:23][CH2:24][CH2:25]2)=[CH:28][CH:29]=1

Komponenten

4

Edukt 1

HCID 541291594-(2,3-dihydro-1,3-dioxo-1H-pyrrolo[3,4-c]pyridin-2-yl)-N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine

Produkt 1

HCID 69844740N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-4-[(3aRS, 7aRS)-(octahydro-1,3-dioxo-1H-pyrrolo[3,4-c]pyridin-2-yl)]-L-phenylalanineAusbeute 13,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6422Trifluoroacetic acidKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 4-(2,3-dihydro-1,3-dioxo-1H-pyrrolo[3,4-c]pyridin-2-yl)-N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine (30 mg, 0.057 mmol) in ethanol (4 mL) containing a few drops of TFA was hydrogenated over 10% Pd(C) (6 mg) for 18 hours. The mixture was filtered and evaporated and the residue was purified by RP-HPLC on a 4×30 cm Rainin C-18 column using a gradient of 5 to 95% acetonitrile:water containing 0.75% trifluoroacetic acid at a flow of 49 mL/min over 35 min. The peak eluting at 59.5% acetonitrile was concentrated and mixture was lyophilized to give N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-4-[(3aRS, 7aRS)-(octahydro-1,3-dioxo-1H-pyrrolo[3,4-c]pyridin-2-yl)]-L-phenylalanine (4.2 mg), HR FABMS: obs. mass 534.2602. Calcd. mass 534.2604 (M+H). The peak eluting at 62% acetonitrile was concentrated and the mixture lyophilzed to give 4-[(RS)-2,3,5,6,7,7a-hexahydro-1,3-dioxo-1H-pyrrolo[3,4-c]pyridin-2-yl]-N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine (4.9 mg), HR FABMS:

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. customthe residue was purified by RP-HPLC on a 4×30 cm Rainin C-18 column
  4. washThe peak eluting at 59.5% acetonitrile
  5. concentrationwas concentrated

Quellen und Nachweise

ORD-Eintrag
ord-fdc751073ebf40639725d6b6872fe328
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06806365B2

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