Pivaloyl chloride → HCID 68870757, compound

HRID 1817878Notes

Reaction equation

HRID 1817878 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH:12][CH2:13][CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[C:5]([O:7][CH3:8])=[O:6].[C:20](Cl)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22]>C(OCC)(=O)C>[CH3:22][C:21]([CH3:24])([CH3:23])[C:20]([NH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH:12][CH2:13][CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[C:5]([O:7][CH3:8])=[O:6])=[O:25]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 57636251HCID 57636251, compound

Product 1

HCID 68870757HCID 68870757, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-amino-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]benzoate (step B, 527 mg, 1.93 mmol) in ethyl acetate (16 mL) was added pivaloyl chloride (256 mg, 2.12 mmol) at room temperature. After stirring for 14 h at room temperature, the mixture was quenched with saturated sodium hydrogencarbonate aqueous solution. The mixture was extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure to afford the title compound (455 mg, 71%) as a white solid.

Workup

  1. customthe mixture was quenched with saturated sodium hydrogencarbonate aqueous solution
  2. extractionThe mixture was extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1c3b9c88902455da4fa7b116757fa41
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

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