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Lithium Hydroxide → (S)-3-methyl-2-(4'-{[3-methyl-4-(3-nitro-phenyl)-benzofuran-2-carbonyl]-amino}-biphenyl-4-sulfonylamino)-butyric acid

HRID 29363
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 29363
C[O:2][C:3](=[O:46])[C@@H:4]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]3[O:28][C:29]4[CH:36]=[CH:35][CH:34]=[C:33]([C:37]5[CH:42]=[CH:41][CH:40]=[C:39]([N+:43]([O-:45])=[O:44])[CH:38]=5)[C:30]=4[C:31]=3[CH3:32])=[O:26])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])[CH:5]([CH3:7])[CH3:6].[Li+].[OH-]>C1COCC1>[CH3:6][CH:5]([CH3:7])[C@H:4]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]([NH:24][C:25]([C:27]3[O:28][C:29]4[CH:36]=[CH:35][CH:34]=[C:33]([C:37]5[CH:42]=[CH:41][CH:40]=[C:39]([N+:43]([O-:45])=[O:44])[CH:38]=5)[C:30]=4[C:31]=3[CH3:32])=[O:26])=[CH:22][CH:23]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:3]([OH:46])=[O:2]
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Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 68714534(S)-3-methyl-2-(4'-{[3-methyl-4-(3-nitro-phenyl)-benzofuran-2-carbonyl]-amino}-biphenyl-4-sulfonylamino)-butyric acid methyl ester

Produkt 1

HCID 11467766(S)-3-methyl-2-(4'-{[3-methyl-4-(3-nitro-phenyl)-benzofuran-2-carbonyl]-amino}-biphenyl-4-sulfonylamino)-butyric acidAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To 41 mg of (S)-3-methyl-2-(4′-{[3-methyl-4-(3-nitro-phenyl)-benzofuran-2-carbonyl]-amino}-biphenyl-4-sulfonylamino)-butyric acid methyl ester dissolved in 0.5 mL of THF was added 2 mL of LiOH solution (3.6 g LiOH/50 mL MeOH/50 mL H2O). The mixture was stirred at room temperature for 4 days. The solvents were removed under vacuum and the residue was dissolved in 5 mL of water. The solution was acidified and the resulting suspension was filtered. The solid product was dried under vacuum to give 29 mg of (S)-3-methyl-2-(4′-{[3-methyl-4-(3-nitro-phenyl)-benzofuran-2-carbonyl]-amino}-biphenyl-4-sulfonylamino)-butyric acid, obtained as pale brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.8 (dd, J=12.4, 6.8 Hz, 6 H) 1.9 (m, 1 H) 2.2 (s, 3 H) 3.6 (dd, J=9.3, 6.1 Hz, 1 H) 7.3 (dd, J=7.3, 0.8 Hz, 1 H) 7.6 (dd, J=8.3, 7.3 Hz, 1 H) 7.8 (m, 8 H) 8.0 (d, J=8.8 Hz, 3 H) 8.1 (d, J=9.3 Hz, 1 H) 8.3 (t, J=1.9 Hz, 1 H) 8.3 (m, 1 H) 10.6 (s, 1 H) 12.6 (s, 1 H).

Aufarbeitung

  1. customThe solvents were removed under vacuum
  2. dissolutionthe residue was dissolved in 5 mL of water
  3. filtrationthe resulting suspension was filtered
  4. customThe solid product was dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-bbd73da0de8242b9881c9a3c904208e5
Quelldatensatz
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07420001B2

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