Dichloromethane → HCID 117839182, compound

HRID 1477633Notes

Reaction equation

HRID 1477633 reaction equation
ClCCl.[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C@H:16]([O:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH:12]=2)=[CH:7][CH:6]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[C:18]([O:17][C@H:16]1[C:11]([C:8]2[CH:9]=[CH:10][C:5]([F:4])=[CH:6][CH:7]=2)=[CH:12][CH2:13][NH:14][CH2:15]1)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 117849117HCID 117849117, compound

Product 1

HCID 117839182HCID 117839182, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a dichloromethane solution (32 mL) of tert-butyl (S)-4-(4-fluorophenyl)-5-(pivaloyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (1.62 g, 4.29 mmol) synthesized in Reference Synthesis Example 136, trifluoroacetic acid (6.5 mL) was added and the resultant mixture was stirred at room temperature for 20 hours. After completion of the reaction, saturated sodium bicarbonate aqueous solution was added to the reaction solution and extraction from the resultant mixture with ethyl acetate was performed. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the title compound as a crude product.

Workup

  1. additionwas added
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2e33c7d0ec64e7ea79556f40daac06f
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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