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

HRID 2121193ノート

反応式

HRID 2121193 の反応式
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

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 9913272HCID 9913272、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-011917e423554a08be64ff0a09b51ae4
出典データセット
uspto-grants-2004_02
特許番号
US06693123B2

反応ノート

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