Lithium hydroxide, monohydrate → [4-(Pyrid-3-ylaminomethyl)-2-phenylbenzoyl]methionine

HRID 2121193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2121193
Cl.C[O:3][C:4](=[O:33])[C@H:5]([CH2:29][CH2:30][S:31][CH3:32])[NH:6][C:7](=[O:28])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:10][C:9]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O.[OH-].[Li+]>C1COCC1.O>[N:18]1[CH:19]=[CH:20][CH:21]=[C:16]([NH:15][CH2:14][C:11]2[CH:12]=[CH:13][C:8]([C:7]([NH:6][C@H:5]([C:4]([OH:33])=[O:3])[CH2:29][CH2:30][S:31][CH3:32])=[O:28])=[C:9]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:10]=2)[CH:17]=1

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 9913272HCID 9913272, Verbindung

Produkt 1

HCID 10478128[4-(Pyrid-3-ylaminomethyl)-2-phenylbenzoyl]methionineAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of [4-(pyrid-3-ylaminomethyl)-2-phenylbenzoyl]methionine methyl ester hydrochloride (72 mg, 0.16 mmol) in THF (3 mL) was added a solution of lithium hydroxide hydrate (13 mg, 0.32 mmol) in water (1 mL) and the reaction mixture was stirred for 30 minutes. The THF was evaporated in vacuo and the residue was taken up in aqueous 3N HCl. The solution was concentrated and the residue was purified by preparative HPLC (70% acetonitrile-0.1% aqueous trifluoroacetic acid) to give [4-(pyrid-3-ylaminomethyl)-2-phenylbenzoyl]methionine (39 mg, 50%). 1H NMR (300 MHz., DMSO-d6) δ 8.48 (d, 1H), 8.17 (m, 1H), 7.97 (m, 1H), 7.56 (m, 2H), 7.29-7.44 (m, 7H), 4.51 (bd, 2H), 4.48 (ddd, 1H), 2.24 (m, 2H), 1.99 (s, 3H), 1.85 (m, 2H). MS (CI NH3) m/e 436 (M+H)+, 418, 319, 287, 194, 165. Anal calcd for C24H25N3O3S (+1.26 TFA): C, 55.00; H, 4.57; N, 7.25. Found: C, 54.97; H, 4.58; N, 7.33.

Aufarbeitung

  1. customThe THF was evaporated in vacuo
  2. concentrationThe solution was concentrated
  3. customthe residue was purified by preparative HPLC (70% acetonitrile-0.1% aqueous trifluoroacetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-011917e423554a08be64ff0a09b51ae4
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06693123B2

Notizen zur Reaktion

Wird geladen…