Hydrochloric Acid → HCID 70664571, compound

HRID 468629Notes

Reaction equation

HRID 468629 reaction equation
[OH-].[Li+].[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:17]([F:18])=[CH:16][N:15]([CH2:19][CH2:20][C@@:21]([CH3:31])([S:27]([CH3:30])(=[O:29])=[O:28])[C:22]([O:24]CC)=[O:23])[C:14](=[O:32])[CH:13]=2)=[CH:8][CH:7]=1)[CH3:4].Cl>O1CCCC1.O>[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:17]([F:18])=[CH:16][N:15]([CH2:19][CH2:20][C@@:21]([CH3:31])([S:27]([CH3:30])(=[O:28])=[O:29])[C:22]([OH:24])=[O:23])[C:14](=[O:32])[CH:13]=2)=[CH:8][CH:7]=1)[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86670640HCID 86670640, compound

Product 1

HCID 70664571HCID 70664571, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide (108 mg, 4.37 mmol) was added to a solution of ethyl (2R)-4-[4-(4-ethoxyphenyl)-5-fluoro-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)butanoate (320 mg, 0.728 mmol) in tetrahydrofuran:water (1:1, 20 mL) and the reaction was allowed to stir at rt until complete. The reaction mixture was acidified with 4 M aq HCl and extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered and concentrated to afford the title compound as a solid (220 mg, 73%). MS (LCMS) m/z 412.2 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.26-1.40 (m, 3H) 1.54 (s, 3H) 2.07-2.26 (m, 1H) 2.43 (d, J=6.24 Hz, 1H) 3.14 (s, 3H) 3.83-4.15 (m, 4H) 6.42 (d, J=7.81 Hz, 1H) 6.93-7.07 (m, 2H) 7.50 (dd, J=8.68, 1.85 Hz, 2H) 7.97 (d, J=6.83 Hz, 1H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8266d1924dcd4222aaf9990d0148fdeb
Source dataset
uspto-grants-2014_01
Patent number
US08624034B2

Reaction notes

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