Water → HCID 9797036, compound

HRID 742360Notes

Reaction equation

HRID 742360 reaction equation
[CH2:1]([C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([N:14]=C=O)[C:4]=1[CH2:17]/[CH:18]=[C:19](\[CH3:26])/[CH2:20][CH2:21][C:22]([O:24]C)=[O:23])[CH3:2].O.O.[OH-].[Li+]>O1CCOCC1>[NH2:14][C:5]1[C:4]([CH2:17]/[CH:18]=[C:19](\[CH3:26])/[CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[C:3]([CH2:1][CH3:2])[C:11]([CH3:12])=[C:10]2[C:6]=1[C:7](=[O:13])[O:8][CH2:9]2

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 86749563HCID 86749563, compound

Product 1

HCID 9797036HCID 9797036, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.0 g of methyl (E)-6-(1,3-dihydro-6-ethyl-4-isocyanato-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate is dissolved in 50 ml of 1,4-dioxane and treated with 16 ml of water and 2.0 g of lithium hydroxide monohydrate. The mixture is stirred at room temperature for 2 hours and then partitioned between aqueous 1N sodium hydrogen sulfate and ethyl acetate. The organic phase is washed twice with water, once with brine, and dried over magnesium sulfate. The solvent is evaporated under reduced pressure and the residue purified by chromatography on silica gel, to give (E)-6-(4-amino-1,3-dihydro-6-ethyl-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic acid.

Workup

  1. custompartitioned between aqueous 1N sodium hydrogen sulfate and ethyl acetate
  2. washThe organic phase is washed twice with water, once with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent is evaporated under reduced pressure
  5. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-dbf18f691cdd49fbac7e8d2791fa4f28
Source dataset
uspto-grants-1996_09
Patent number
US05554612

Reaction notes

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