Potassium Carbonate → Tert-butyl[2-(5-ethyloxycarbonyl-pentylsulfanyl)-benzoimidazol-1-yl]-acetate

HRID 2389473Notes

Reaction equation

HRID 2389473 reaction equation
[SH:1][C:2]1[N:6]([CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=1.[CH2:19]([O:21][C:22](=[O:29])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Br)[CH3:20].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:11]([O:10][C:8](=[O:9])[CH2:7][N:6]1[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=[C:2]1[S:1][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:29])([CH3:13])([CH3:14])[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 117544Ethyl 6-bromohexanoateHCID 178451223HCID 178451223, compound

Product 1

HCID 90987543Tert-butyl[2-(5-ethyloxycarbonyl-pentylsulfanyl)-benzoimidazol-1-yl]-acetateYield 67.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of tert-butyl (2-mercapto-benzoimidazol-1-yl)-acetate (Intermediate 3-I, 52 mg, 0.2 mmol), 6-bromo-hexanoic acid ethyl ester (49 mg, 39 μl, 0.22 mmol) and K2CO3 (55 mg, 0.4 mmol) is refluxed in acetone (2 ml) for 5 h and stirred at rt overnight. Evaporation of the solvent in vacuo affords a residue that is purified by flash-chromatography on silica-gel (AcOEt/heptane, 25:75), yielding the title compound (55 mg) in 68% as a colourless oil: tR=7.24 min (LC-1), ESI-MS (pos.): m/z 407.23 [M+H]+, ESI-MS (neg.) 405.22 [M−H]+; 1H-NMR (CDCl3): δ (ppm) 1.25 (t, 3H CH3), 1.44 (s, 9H, tBu), 1.48 (m, 2H), 1.66 (quint., 2H), 1.79 (quint., 2H), 2.30 (t, 2H, CH2C═O), 3.38 (t, 2H, SCH2), 4.10 (q, 2H, OCH2), 4.73 (s, 2H, CH2CO2), 7.17-7.25 (m, 3Harom), 7.69 (m, 1Harom).

Workup

  1. customEvaporation of the solvent in vacuo
  2. customaffords a residue that
  3. customis purified by flash-chromatography on silica-gel (AcOEt/heptane, 25:75)

Sources & evidence

ORD record
ord-105e05a2312545f28008739612e50b19
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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