Lithium Hydroxide → HCID 59799842, compound

HRID 1094454Notes

Reaction equation

HRID 1094454 reaction equation
C[O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[CH2:10][C@@H:11]1[O:15][C:14]([CH3:17])([CH3:16])[N:13]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:12]1[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32].[OH-].[Li+].S(=O)(=O)(O)[O-].[Na+]>O1CCOCC1.O>[C:21]([O:20][C:18]([N:13]1[C@H:12]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[F:32])[C@H:11]([CH2:10][C:5]2[N:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([OH:33])=[O:2])[O:15][C:14]1([CH3:17])[CH3:16])=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 516919Sodium BisulfateHCID 66639408HCID 66639408, compound

Product 1

HCID 59799842HCID 59799842, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of 2-[(4R,5S)-3-tert-butoxycarbonyl-4-(2-fluoro-benzyl)-2,2-dimethyl-oxazolidin-5-ylmethyl]-nicotinic acid methyl ester (5.5 g, 12 mmol) in 100 mL of dioxane/water (2:1) is added lithium hydroxide (0.57 g, 24 mmol). The reaction is stirred at room temperature for 2 hr after which time the reaction is diluted and the pH adjusted to pH 4-5 with a 2M solution of sodium bisulfate. The product is extracted into dichloromethane and the combined organic phases are dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification of the resultant residue by silica gel flash column chromatography gives the title compound.

Workup

  1. additionis diluted
  2. extractionThe product is extracted into dichloromethane
  3. dry with materialthe combined organic phases are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the resultant residue by silica gel flash column chromatography

Sources & evidence

ORD record
ord-f6d1120918ca40c69c82f22371083c40
Source dataset
uspto-grants-2012_03
Patent number
US08133907B2

Reaction notes

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