Lithium Hydroxide → HCID 178524247、化合物

HRID 711318ノート

反応式

HRID 711318 の反応式
C[O:2][C:3]([C:5]1[C:13]2[NH:12][C:11]([C:14]3[C:15](=[O:30])[NH:16][CH:17]=[CH:18][C:19]=3[NH:20][CH2:21][C@@H:22]([OH:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[Li+].[OH-].C1COCC1>O>[OH:29][C@@H:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:21][NH:20][C:19]1[CH:18]=[CH:17][NH:16][C:15](=[O:30])[C:14]=1[C:11]1[NH:12][C:13]2[C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=[CH:8][C:9]=2[N:10]=1

参加物

5

反応物 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 178497576HCID 178497576、化合物

生成物 1

HCID 178524247HCID 178524247、化合物収率 102.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

In a 200 mL round-bottomed flask, 2-[4-((S)-2-hydroxy-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-3H-benzoimidazole-4-carboxylic acid methyl ester (0.87 g, 2.15 mmol) and LiOH (258 mg, 10.8 mmol) were combined with THF (20 mLl) and Water (5 mL) to give a purple suspension. The reaction was stirred at room temperature overnight. The next day the reaction was heated in dry block at 50° C. for 3.5 hr and cooled to room temperature. The reaction was dilute with water, concentrated, dilute with more water, and acidify with 1M HCl, and filtered. The resulting solid was washed with water and hexanes, and dried over house vacuum yielding 2-[4-((S)-2-hydroxy-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-3H-benzoimidazole-4-carboxylic acid (0.86 g, 102% yield) as a purple solid. LC/MS calcd for C21H18N4O4 (m/e) 390.0, obsd 391.2 (M+H); 1H NMR; (DMSO-d6): 13.35 (s, 1H), 11.19 (d, J=6.0 Hz, 1H), 10.97 (t, J=4.9 Hz, 1H), 7.75 (dd, J=7.7, 3.9 Hz, 2H), 7.56 (d, J=7.3 Hz, 2H), 7.22-7.44 (m, 5H), 6.20 (d, J=7.5 Hz, 1H), 5.80 (br. s., 1H), 4.92 (t, J=5.5 Hz, 1H), 3.54-3.74 (m, 3H).

後処理

  1. customto give a purple suspension
  2. temperatureThe next day the reaction was heated in dry block at 50° C. for 3.5 hr
  3. temperaturecooled to room temperature
  4. concentrationconcentrated
  5. additiondilute with more water
  6. filtrationfiltered
  7. washThe resulting solid was washed with water and hexanes
  8. customdried over house vacuum

出典と根拠

ORDレコード
ord-731f5111f5b2400f87522ed1a303f0e4
出典データセット
uspto-grants-2015_11
特許番号
US09181218B2

反応ノート

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