Pivaloyl chloride → HCID 67357580, compound

HRID 1927559Notes

Reaction equation

HRID 1927559 reaction equation
[C:1]([N:8]1[CH2:12][C@@H:11]([NH:13][CH:14]2[CH2:19][CH2:18][C:17]([F:21])([F:20])[CH2:16][CH2:15]2)[CH2:10][C@H:9]1[C:22]([O:24][CH3:25])=[O:23])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:26](Cl)(=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28]>ClCCCl.CN(C1C=CN=CC=1)C>[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([CH:14]2[CH2:19][CH2:18][C:17]([F:20])([F:21])[CH2:16][CH2:15]2)[C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:10][C@H:9]1[C:22]([O:24][CH3:25])=[O:23])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 67358561HCID 67358561, compound

Product 1

HCID 67357580HCID 67357580, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

Methyl (2S,4S)-1-BOC-4-[(4,4-difluorocyclohexyl)amino]pyrrolidine-2-carboxylate (1.03 g, 2.84 mmol) obtained in Step A was dissolved in DCE (5 mL) and TEA (5 mL) and DMAP (0.36 g, 2.84 mmol) were added thereto. Commercially available pivaloyl chloride (1.03 g, 8.52 mmol) was also added thereto. The reaction solution was heated to 90° C. and stirred for 24 hours. After the reaction was completed, the solvent was removed in vacuo and saturated NaHCO3 aqueous solution was added. The solution was extracted with EtOAc. The extracted organic solution was washed with 1N HCl solution, dried over MgSO4, concentrated in vacuo and purified by column chromatography (eluent: EtOAc/Hex=1/4) to give the title compound (1.04 g, 82%).

Workup

  1. customthe solvent was removed in vacuo and saturated NaHCO3 aqueous solution
  2. additionwas added
  3. extractionThe solution was extracted with EtOAc
  4. washThe extracted organic solution was washed with 1N HCl solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography (eluent: EtOAc/Hex=1/4)

Sources & evidence

ORD record
ord-5223796cb0ae44d3b598d6656b5c921c
Source dataset
uspto-grants-2012_05
Patent number
US08183243B2

Reaction notes

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