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

HRID 2389469노트

반응식

HRID 2389469 반응식
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]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 814952-(Chloromethyl)anisoleHCID 178451223HCID 178451223, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-086a1f7b873e419c8bfdb9b685b6f8f0
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273740B2

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