Pivalic acid → HCID 57636260, compound

HRID 1817879Notes

Reaction equation

HRID 1817879 reaction equation
[CH3:1][C:2]([CH3:25])([CH3:24])[C:3]([NH:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[NH:16][CH2:17][CH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[C:9]([O:11][CH3:12])=[O:10])=O.C(O)(=O)C(C)(C)C>ClCCl>[C:2]([C:3]1[N:16]([CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:15]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=2[N:5]=1)([CH3:25])([CH3:24])[CH3:1]

Participants

4

Reactant 2

HCID 6417Pivalic acidHCID 68870757HCID 68870757, compound

Product 1

HCID 57636260HCID 57636260, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 3-[(2,2-dimethylpropanoyl)amino]-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]benzoate (step C, 455 mg, 1.31 mmol) and pivalic acid (2.20 g, 21.5 mmol) was stirred at 120° C. for 12 h. After cooling to room temperature, the mixture was diluted with dichloromethane. The solution was washed with 1N sodium hydroxide aqueous solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1 as eluent) to afford the title compound (327 mg, 76%) as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. washThe solution was washed with 1N sodium hydroxide aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1 as eluent)

Sources & evidence

ORD record
ord-df7d45e97c68460eb16d1772c0c78475
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

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