Tetrahydrofuran → Ethyl hexanoate

HRID 1747393Notes

Reaction equation

HRID 1747393 reaction equation
NC1C=CC2N([CH:22]([CH2:27][CH2:28][CH3:29])[CH2:23][C:24]([OH:26])=[O:25])C(=O)N(CC3C4C(=CC=CC=4C)N(C)C=3)C=2C=1.[Si](N=C=O)(C)(C)C.C(=O)(O)[O-].[Na+].[CH2:44]1COC[CH2:45]1>>[CH2:44]([O:26][C:24](=[O:25])[CH2:23][CH2:22][CH2:27][CH2:28][CH3:29])[CH3:45]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 70696Trimethylsilyl isocyanateHCID 516892Sodium BicarbonateHCID 67359356HCID 67359356, compound

Product 1

HCID 31265Ethyl hexanoate

Procedure

To a solution of 3-[5-Amino-3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]hexanoic acid: ethyl ester (50 mg, 0.111 mmol) in THF (30 ml) was added TMS isocynate (1.73 mg, 15 mmol). The solution was stirred at RT for 3 hours. The reaction was checked by LCMS. To the reaction mixture an aqeous solution of Sodium bicarbonate (60 ml) was added. The resulting mixture, stirred for another 30 minutes, was then extracted with Ethyl Acetate. The organic layer, dried over MgSO4, was filtered and evaporated to dryness to give a dark residue. The residue was purified by prep TLC, eluded with 10% methanol in Dichloromethane to give 10 mg (18%) of 3-[3-1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-5-ureido-2,3-dihydro-benzoimidazol-1-yl]hexanoic acid ethyl ester. LCMS (ESMS): m/z 491.58 (M+H).

Workup

  1. stirringThe resulting mixture, stirred for another 30 minutes
  2. extractionwas then extracted with Ethyl Acetate
  3. dry with materialThe organic layer, dried over MgSO4
  4. filtrationwas filtered
  5. customevaporated to dryness
  6. customto give a dark residue
  7. customThe residue was purified by prep TLC

Sources & evidence

ORD record
ord-cf6bf342643944f6b1785d10f3593f0d
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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