Sodium Hydroxide → HCID 9837149, compound

HRID 398985Notes

Reaction equation

HRID 398985 reaction equation
C([CH2:4][C@H:5]1[C@@H:9]([CH3:10])[O:8][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[N:6]1)(O)=O.[OH-:17].[Na+].C[OH:20].C(Cl)(Cl)Cl>CO>[CH3:10][C@H:9]1[O:8][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[N:6][C@@H:5]1[C:4]([OH:20])=[O:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21584188Chloroform methanolHCID 57251745HCID 57251745, compound

Product 1

HCID 9837149HCID 9837149, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (4S, 5R)-4-carboxymethyl-4,5-dihydro-5-methyl-2-(2-pyridinyl)oxazole (0.22 g, 1.00 mmol, obtained as above) in MeOH (2 mL) was added aq NaOH (44.0 mg, 1.10 mmol in 0.20 mL of H2O ). After 1 h at room temperature, the solvent was removed under reduced pressure. The residue was partitioned between EtOAc (5 mL) and 1N HCl (1 mL). The aqueous layer was extracted with further EtOAc (2×10 mL). the combined organic extracts were dried over MgSO4 and concentrated to give a white residue. Flash chromatography (2% to 10% MeOH/CHCl3 +1% AcOH, silica gel) gave 80.0 mg (39%) of the desired compound as a white solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between EtOAc (5 mL) and 1N HCl (1 mL)
  3. extractionThe aqueous layer was extracted with further EtOAc (2×10 mL)
  4. dry with materialthe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated
  6. customto give a white residue

Sources & evidence

ORD record
ord-1646ceaf36e9411991d1630b6e9c9944
Source dataset
uspto-grants-1998_10
Patent number
US05817680

Reaction notes

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