Tetrahydrofuran → HCID 178501110, compound

HRID 538032Notes

Reaction equation

HRID 538032 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][NH:12][C:13](=[O:21])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH2:20])[CH2:7][CH2:6]1)=[O:4].C1C[O:25][CH2:24]C1>>[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][CH2:7][C@H:8]([CH2:11][N:12]2[C:13](=[O:21])[C:14]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:20][C:24]2=[O:25])[CH2:9][CH2:10]1)=[O:4]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 178501125HCID 178501125, compound

Product 1

HCID 178501110HCID 178501110, compoundYield 97%

Procedure

To a solution of 1,1-carbonyldiimidazole (17 g, 103.5 mmol) in THF (200 mL), trans-4-[(2-Amino-benzoylamino)-methyl]-cyclohexanecarboxylic acid methyl ester (15 g, 51.72 mmol) was added and the reaction was heated to reflux temperature for 16 hours. The mixture was allowed to cool down to room temperature and the solvent was removed under reduced pressure. The residue was washed with 100 mL of H2O and the precipitate was filtered. The tiled compound (15.9 g, yield 97%) was obtained as a white solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux temperature for 16 hours
  3. customthe solvent was removed under reduced pressure
  4. washThe residue was washed with 100 mL of H2O
  5. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-04fe1bcd178b429e85faa69700609754
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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