Pivaloyl chloride → HCID 68614758, compound

HRID 1817894Notes

Reaction equation

HRID 1817894 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][C:11]1([OH:16])[CH2:15][CH2:14][CH2:13][CH2:12]1.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>C(OCC)(=O)C>[Br:8][C:6]1[CH:5]=[CH:4][C:3]([NH:9][CH2:10][C:11]2([OH:16])[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:2]([NH:1][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:7]=1

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 65103218HCID 65103218, compound

Product 1

HCID 68614758HCID 68614758, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-{[(2-amino-4-bromophenyl)amino]methyl}cyclopentanol (Step B of Example 34, 1.3 g, 4.15 mmol) in ethyl acetate (100 mL) was added pivaloyl chloride (511 mg, 4.15 mmol) at room temperature. After stirring for 2 h at room temperature, the mixture was quenched with saturated sodium hydrogencarbonate aqueous solution. The mixture was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 as eluent) to afford the title compound (1.3 g, 75%) as a beige amorphous solid.

Workup

  1. customthe mixture was quenched with saturated sodium hydrogencarbonate aqueous solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1 as eluent)

Sources & evidence

ORD record
ord-52bca023e29e442899ad835a1c4811b1
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

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