Benzylamine → Methyl 5-((benzylcarbamoyloxy)methyl)-3-phenylthiophene-2-carboxylate

HRID 1186713Notes

Reaction equation

HRID 1186713 reaction equation
[OH:1][CH2:2][C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=1.[C:18]([N:25]1[CH:29]=[CH:28]N=C1)(N1C=CN=C1)=[O:19].C(N)[C:31]1[CH:36]=[CH:35]C=[CH:33][CH:32]=1.N12CCCN=C1CCCCC2>C1COCC1.C(OCC)(=O)C>[CH2:29]([NH:25][C:18]([O:1][CH2:2][C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=1)=[O:19])[C:28]1[CH:35]=[CH:36][CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58121059Methyl 5-(hydroxymethyl)-3-phenylthiophene-2-carboxylate

Product 1

HCID 58121088Methyl 5-((benzylcarbamoyloxy)methyl)-3-phenylthiophene-2-carboxylateYield 82%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 169 (0.900 g, 3.62 mmol) in THF was added 1,1′-carbonyldiimidazole (0.588 g, 3.62 mmol) and stirred at room temperature for 90 min. Then BnNH2 (0.396 mL, 3.62 mmol), TEA (0.505 mL, 3.62 mmol) and 1,8-Diazabicyclo[5.4.0]undec-7-ene (0.546 mL, 3.62 mmol) were added and stirred at room temperature for an additional 2 hours. The reaction mixture was diluted with ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered and concentrated under vacuum. The residue was purified by ISCO (40 g column, 0-45% ethyl acetate in hexanes) to yield in 82% (1.13 g) compound 170 as a pink solid.

Workup

  1. stirringstirred at room temperature for an additional 2 hours
  2. washwashed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by ISCO (40 g column, 0-45% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d8c6c6a16aff447aa367b180d14630d8
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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