Methyl iodide → Methyl 5-((benzyl(methyl)carbamoyloxy)methyl)-3-phenylthiophene-2-carboxylate

HRID 1186714Notes

Reaction equation

HRID 1186714 reaction equation
[CH2:1]([NH:8][C:9]([O:11][CH2:12][C:13]1[S:17][C:16]([C:18]([O:20][CH3:21])=[O:19])=[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:30]I>C1COCC1>[CH2:1]([N:8]([CH3:30])[C:9]([O:11][CH2:12][C:13]1[S:17][C:16]([C:18]([O:20][CH3:21])=[O:19])=[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:14]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58121088Methyl 5-((benzylcarbamoyloxy)methyl)-3-phenylthiophene-2-carboxylate

Product 1

HCID 58121161Methyl 5-((benzyl(methyl)carbamoyloxy)methyl)-3-phenylthiophene-2-carboxylateYield 53.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 170 (0.620 g, 1.625 mmol) in 10 mL of THF was added NaH (0.098 g, 2.438 mmol) and stirred at room temperature for 20 min. Then MeI (0.5 ml, 8.00 mmol) was added and stirred for an additional 2 hours at 50° C. The reaction mixture was cooled down at room temperature, quenched with 2 mL of MeOH, diluted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by ISCO (40 g column, 5%-30% ethyl acetate in hexanes) to yield in 53% (342 mg) compound 171 as colorless oil.

Workup

  1. stirringstirred for an additional 2 hours at 50° C
  2. temperatureThe reaction mixture was cooled down at room temperature
  3. customquenched with 2 mL of MeOH
  4. additiondiluted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by ISCO (40 g column, 5%-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ce208eadb7964ba1a79cb319cfbf8f5e
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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