Lithium Hydroxide → PYR412

HRID 1668411Notes

Reaction equation

HRID 1668411 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14](N2[C@@H](CC3C=CC=CC=3)COC2=O)=[O:15])[N:9]1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-:37]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]([OH:37])=[O:15])[N:9]1[C:29]([O:31][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:30])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 11016430HCID 11016430, compound

Product 1

HCID 10871237PYR412

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-3-((S)-4-benzyl-2-oxo-oxazolidine-3-carbonyl)-tetrahydro-pyridazine-1,2-dicarboxylic acid di-tert-butyl ester (1.22 g, 2.5 mmol) in THF (15 mL) at 0° C., is added a solution of LiOH (7 mL, 5% in H2O). After stirring at 0° C. for 2 hours, the reaction mixture is diluted with 15 mL of water and extracted with 20 mL of ether. The ether layer is extracted with 10 mL of saturated NaHCO3. The combined aqueous layers is acidified with saturated NaHSO4 to Ph=2, and extracted with CH2Cl2 (3×20 mL). The combined organic layers is dried over Na2SO4 and concentrated to give clued product (0.83 g) as a pale gum without further purification for next step reaction. (NMR and MS data confirmed, U-3133-56-22).

Workup

  1. extractionextracted with 20 mL of ether
  2. extractionThe ether layer is extracted with 10 mL of saturated NaHCO3
  3. extractionextracted with CH2Cl2 (3×20 mL)
  4. dry with materialThe combined organic layers is dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-537e29ecff1d409e9192ced841af3eac
Source dataset
uspto-grants-2011_08
Patent number
US07989441B2

Reaction notes

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