Acetic Acid → HCID 71060280, compound

HRID 1036716Notes

Reaction equation

HRID 1036716 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:21](=[O:23])[NH2:22])([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:24](OCC)(OCC)OCC.C(O)(=O)C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]2([N:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:24]=[N:22][C:21]2=[O:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 31214Ethyl orthoformateHCID 710601663-Carbamoyl-3-phenylamino-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 71060280HCID 71060280, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-carbamoyl-3-phenylamino-piperidine-1-carboxylic acid tert-butyl ester (300 mg, 0.94 mmol) in toluene (10 ml) was added triethyl orthoformate (0.47 ml, 2.8 mmol) and acetic acid (0.5 ml, 8.7 mmol). The mixture was heated at reflux overnight. The reaction mixture was cooled and washed with a saturated solution of sodium bicarbonate (25 ml). The organics were separated and the aqueous extracted with EtOAc (10 ml). The organics portions were combined, dried (MgSO4) and concentrated in vacuo to afford an oil. Purification of the crude product by chromatography on silica eluting with 0-50% EtOAc in iso-hexane afforded the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureThe reaction mixture was cooled
  4. washwashed with a saturated solution of sodium bicarbonate (25 ml)
  5. customThe organics were separated
  6. extractionthe aqueous extracted with EtOAc (10 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto afford an oil
  10. customPurification of the crude product by chromatography on silica eluting with 0-50% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-8a2f1589726f4deb9ad1e57781d3c575
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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