Reaktion #81108

ord-bb7c5a94980843fb971b42e63570f238

Reaktionsgleichung

CC(C)[C@H](NC(=O)CNC(=O)OC(C)(C)C)C(=O)N[C@@H](Cc1ccccc1)C(O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)CNC(=O)OC(C)(C)C)C(C)C
resultant compound
CC(C)[C@H](NC(=O)CNC(=O)OC(C)(C)C)C(=O)N[C@@H](Cc1ccccc1)C(O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)CNC(=O)OC(C)(C)C)C(C)C
(2S,4S)-2,4-Bis-(N-(N-(Boc-glycinyl)valinyl)amino)-1,5-diphenyl-3-hydroxypentane
CO
methanol
→
CC(C)[C@H](NC(=O)CN)C(=O)N[C@@H](Cc1ccccc1)C(O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)CN)C(C)C
desired compound
Ausbeute 91.0%
CC(C)[C@H](NC(=O)CN)C(=O)N[C@@H](Cc1ccccc1)C(O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)CN)C(C)C
(2S,4S)-2,4-Bis-(N-(N-(glycinyl)valinyl)amino)-1,5-diphenyl-3-hydroxypentane
Ausbeute 91.0%

Edukte

—
resultant compound
CC(C)[C@H](NC(=O)CNC(=O)OC(C)(C)C)C(=O)N[C@@H](Cc1ccccc1)C(O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)CNC(=O)OC(C)(C)C)C(C)C
resultant compound
CC(C)[C@H](NC(=O)CNC(=O)OC(C)(C)C)C(=O)N[C@@H](Cc1ccccc1)C(O)[C@H](Cc1ccccc1)NC(=O)[C@@H](NC(=O)CNC(=O)OC(C)(C)C)C(C)C
(2S,4S)-2,4-Bis-(N-(N-(Boc-glycinyl)valinyl)amino)-1,5-diphenyl-3-hydroxypentane
CO
methanol

Reagenzien

Keine

Lösungsmittel

ClCCl
dichloromethane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeprovided

Vorschrift

Using the procedure of Example 6F but replacing the resultant compound of Example 6E with the resultant compound of Example 140 provided, after silica gel chromatography using 10% methanol in dichloromethane, 48.7 mg (91%) of the desired compound as a white solid. 1H NMR (DMSO-d6) δ 0.70-0.83 (four d, 12H), 1.78 (m, 1H), 1.96 (m, 1H), 2.62 (m, 2H), 2.74 (br d, 2H), 2.97 (m, 1H), 3.46-3.87 (m, 5H), 4.02 (m, 2H), 4.21 (m, 1H), 5.33 (br d, 1H), 7.08-7.26 (m, 10H), 7.57 (br d, 2H), 7.67 (br d, 1H), 7.86 (br d, 1H). Mass spectrum: (M+H)+ =583.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05616714uspto-grants-1997_04