Sodium Hydroxide → HCID 69855094, compound

HRID 987925Notes

Reaction equation

HRID 987925 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH2:20][CH:21]2[CH:26]([C:27]([O:29]CC)=[O:28])[CH2:25][CH:24]=[CH:23][CH2:22]2)[O:10][C:9]1([CH3:33])[CH3:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C.O>[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:11]([CH2:20][CH:21]2[CH:26]([C:27]([OH:29])=[O:28])[CH2:25][CH:24]=[CH:23][CH2:22]2)[O:10][C:9]1([CH3:33])[CH3:32])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69853448HCID 69853448, compound

Product 1

HCID 69855094HCID 69855094, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-benzyl-5-(6-ethoxycarbonyl-cyclohex-3-enylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (4.72 g) in ethanol (80 ml) was treated with a solution of sodium hydroxide (0.82 g) in water (15 ml) and the resulting solution refluxed for 18 hours. The ethanol was then evaporated and the residue partitioned between water and ethyl acetate. The organic solution was washed with saturated sodium chloride solution, dried (anhydrous magnesium sulfate) and evaporated. The residue was subjected to flash chromatography on silica gel eluting with hexane/ethyl acetate (2:1) to afford 4-benzyl-5-(6-carboxy-cyclohex-3-enylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (3.32 g, 75%) Mass spectrum 430 [M+H]+.

Workup

  1. temperaturethe resulting solution refluxed for 18 hours
  2. customThe ethanol was then evaporated
  3. customthe residue partitioned between water and ethyl acetate
  4. washThe organic solution was washed with saturated sodium chloride solution
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. customevaporated

Sources & evidence

ORD record
ord-403d468c11be4850870a7dbbcbcc1f49
Source dataset
uspto-grants-2003_10
Patent number
US06632826B1

Reaction notes

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