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Methanol → 3-(1-(4-bromobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoic acid

HRID 2178429
ノート
印刷プレビュー

反応式

HRID 2178429 の反応式
[Li+].[OH-].[Br:3][C:4]1[CH:40]=[CH:39][C:7]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][C:16]([O:18][CH2:19][C:20]4[CH:29]=[CH:28][C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:21]=4)=[CH:17][C:12]=3[N:11]=[C:10]2[CH2:30][C:31]([CH3:38])([CH3:37])[C:32]([O:34]CC)=[O:33])=[CH:6][CH:5]=1.C1COCC1.CO>O>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][C:16]([O:18][CH2:19][C:20]4[CH:29]=[CH:28][C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:21]=4)=[CH:17][C:12]=3[N:11]=[C:10]2[CH2:30][C:31]([CH3:37])([CH3:38])[C:32]([OH:34])=[O:33])=[CH:39][CH:40]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 90415263ethyl 3-(1-(4-bromobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoate

生成物 1

HCID 862813933-(1-(4-bromobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoic acid収率 83%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
80 °C

実験手順

A solution of LiOH (39 mg, 0.9 mmol) in water (2 mL) was added to a 20 mL round-bottomed flask containing ethyl 3-(1-(4-bromobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoate (106 mg, 0.19 mmol), THF (3 mL), MeOH (3 mL), and water (3 mL). The resulting solution was heated to 80° C. After 2 h, the solution was concentrated to dryness and the residue was treated with sat. ammonium chloride (20 mL) and EtOAc (20 mL). The organic layer was separated and the aqueous layer was further extracted with EtOAc (2×20 mL). The combined organic layers were dried with sodium sulfate, filtered, and concentrated to dryness. The residue was subjected to FCC to give the title compound (84 mg, 83%). MS (ESI): mass calcd. for C29H26BrN3O3, 543.12; m/z found, 544.2 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 9.00 (d, J=8.7, 1H), 8.32 (d, J=8.5, 1H), 8.26 (d, J=8.4, 1H), 8.15-8.08 (m, 2H), 7.94-7.88 (m, 1H), 7.59 (d, J=8.8, 1H), 7.57-7.51 (m, 3H), 7.41 (dd, J=9.1, 2.4, 1H), 7.19 (d, J=8.6, 2H), 5.82 (s, 2H), 5.76 (s, 2H), 3.53 (s, 2H), 1.42 (s, 6H).

後処理

  1. concentrationthe solution was concentrated to dryness
  2. additionthe residue was treated with sat. ammonium chloride (20 mL) and EtOAc (20 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was further extracted with EtOAc (2×20 mL)
  5. dry with materialThe combined organic layers were dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-bcb5c366ae8547909697fa0c6d24a835
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09067917B2

反応ノート

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