Potassium Carbonate → Tert-butyl[2-(2-methoxy-benzylsulfanyl)-benzoimidazol-1-yl]-acetate

HRID 2389469ノート

反応式

HRID 2389469 の反応式
C([O-])([O-])=O.[K+].[K+].[SH:7][C:8]1[N:12]([CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:11]2[CH:21]=[CH:22][CH:23]=[CH:24][C:10]=2[N:9]=1.[CH3:25][O:26][C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH2:29]Cl>CC(C)=O>[C:17]([O:16][C:14](=[O:15])[CH2:13][N:12]1[C:11]2[CH:21]=[CH:22][CH:23]=[CH:24][C:10]=2[N:9]=[C:8]1[S:7][CH2:29][C:28]1[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=1[O:26][CH3:25])([CH3:19])([CH3:20])[CH3:18]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 814952-(Chloromethyl)anisoleHCID 178451223HCID 178451223、化合物

生成物 1

HCID 90907082Tert-butyl[2-(2-methoxy-benzylsulfanyl)-benzoimidazol-1-yl]-acetate収率 63.8%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A suspension of K2CO3 (31.4 mg, 0.23 mmol) in acetone (3 ml) containing tert-butyl (2-mercapto-benzoimidazol-1-yl)-acetate (Intermediate 3-I, 30 mg, 0.11 mmol) and 2-methoxybenzyl chloride (17.8 mg, 15.8 μl, 0.11 mmol) is stirred at rt overnight. Filtration over Celite and evaporation of the solvent in vacuo affords the pure title compound (27 mg) in 62% yield as a yellow oil: tR=7.47 min (LC-1), MS (pos.): m/z 385.20 [M+H]+; 1H NMR (DMSO-d6): δ (ppm) 1.37 (s, 9H, tBu), 3.90 (s, 3H, OCH3), 4.53 (s, 2H, SCH2), 4.92 (s, 2H, CH2CO2), 6.87 (t, 1Harom), 7.03 (d, 1Harom), 7.21 (m, 2Harom), 7.28 (t, 1Harom), 7.40 (d, 1Harom), 7.50 (m, 1Harom), 7.64 (m, 1Harom).

後処理

  1. filtrationFiltration
  2. customover Celite and evaporation of the solvent in vacuo

出典と根拠

ORDレコード
ord-086a1f7b873e419c8bfdb9b685b6f8f0
出典データセット
uspto-grants-2012_09
特許番号
US08273740B2

反応ノート

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