Sodium Hydroxide → HCID 58585480, compound

HRID 457918Notes

Reaction equation

HRID 457918 reaction equation
[OH-].[Na+].N1CCC[C@H]1C(O)=O.[CH3:11][O:12][N:13]=[C:14]1[CH2:18][N:17]([C:19]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[CH3:33])=[CH:23][CH:22]=2)=[O:20])[C@H:16]([C:34]([O:36]C)=[O:35])[CH2:15]1.O1CCOCC1>O>[CH3:11][O:12][N:13]=[C:14]1[CH2:18][N:17]([C:19]([C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[CH3:33])=[CH:25][CH:26]=2)=[O:20])[C@H:16]([C:34]([OH:36])=[O:35])[CH2:15]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 145742L-ProlineHCID 58715120HCID 58715120, compound

Product 1

HCID 58585480HCID 58585480, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of sodium hydroxide (73 mg, 1.81 mmol) in water (1.2 ml) was added to a proline oximether methyl ester derivative, e.g. methyl (2S,4 EZ)-4-(methoxyimino)-1-[(2′-methyl[1,1′-biphenyl]-4-yl)carbonyl]-2-pyrrolidinecarboxylate (391 mg, 1.1 mmol) in 3:1 dioxane:water (12 ml) and the reaction stirred for 3 h. The reaction mixture was then washed with diethyl ether (2×10 ml), and the aqueous phase acidified to pH 2 (0.1N HCl) and extracted into ethyl acetate. The ethyl acetate layer was then dried over magnesium sulfate, filtered and the solvent was then removed in vacuo to give the desired product, e.g. (2S,4EZ)-4-(methoxyimino)-1-[(2′-methyl[1,1′-biphenyl]-4-yl)carbonyl]-2-pyrrolidinecarboxylic acid in 91% yield as an oil which was used without further purification.

Workup

  1. washThe reaction mixture was then washed with diethyl ether (2×10 ml)
  2. extractionextracted into ethyl acetate
  3. dry with materialThe ethyl acetate layer was then dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was then removed in vacuo

Sources & evidence

ORD record
ord-461154f8bdb04e72938501f6451302c7
Source dataset
uspto-grants-2007_03
Patent number
US07189754B2

Reaction notes

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