2-Propanol, 2-methyl-, lithium salt (1:1) → (S)-N-((3-(3-fluoro-4-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

HRID 1844506Notes

Reaction equation

HRID 1844506 reaction equation
C([O:8][C:9](=[O:29])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[N:18]2)=[C:13]([F:28])[CH:12]=1)C1C=CC=CC=1.[CH3:30][C:31](C)([O-:33])C.[Li+]>C(OCC)(=O)C>[F:28][C:13]1[CH:12]=[C:11]([N:10]2[CH2:13][C@H:12]([CH2:11][NH:10][C:31](=[O:33])[CH3:30])[O:8][C:9]2=[O:29])[CH:16]=[CH:15][C:14]=1[N:17]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[N:18]1

Participants

4

Reactant 2

HCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)HCID 867193723-Fluoro-4-(3-(2-pyridyl)-1-pyrazolyl)phenyl carbamic acid benzyl ester

Product 1

HCID 71477482(S)-N-((3-(3-fluoro-4-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamideYield 91.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The above-described product 20a (1.235 g, 3.18 mmol) and lithium tert-butoxide (0.762 g) were mixed in a reaction vessel. After the air in the vessel was purged with nitrogen, tetrahydrofuran (5 mL) was added into the vessel and the mixture was cooled in an ice-water bath for 5 minutes. Then, methanol (0.204 g, 0.258 mL) was added. Two minutes later, a solution of Compound (11) (1.237 g) in tetrahydrofuran (5 mL) was added. Then, the water-ice bath was removed and the resultant mixture was reacted for 14 hours at room temperature. After completion of the reaction, ethyl acetate was added to the reactant mixture, resulting in a substantial amount of precipitate. Thus obtained mixture was suction-filtered, and the filter cake was recrystallized with a solvent mixture of ethyl acetate/petroleum ether to afford the product 12a (575 mg) as a white powder, with a yield of 45.7%.

Workup

  1. customAfter the air in the vessel was purged with nitrogen, tetrahydrofuran (5 mL)
  2. additionwas added into the vessel
  3. temperaturethe mixture was cooled in an ice-water bath for 5 minutes
  4. additionThen, methanol (0.204 g, 0.258 mL) was added
  5. additionTwo minutes later, a solution of Compound (11) (1.237 g) in tetrahydrofuran (5 mL) was added
  6. customThen, the water-ice bath was removed
  7. customthe resultant mixture was reacted for 14 hours at room temperature
  8. additionwas added to the reactant mixture
  9. customresulting in a substantial amount of precipitate
  10. filtrationThus obtained mixture was suction-filtered
  11. customthe filter cake was recrystallized with a solvent mixture of ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-70789bf2398049c994aa31fb573d5b04
Source dataset
uspto-grants-2015_02
Patent number
US08946436B2

Reaction notes

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