Water → HCID 9948928, compound

HRID 1735795Notes

Reaction equation

HRID 1735795 reaction equation
[N:1]([C:4]1[C:12]([CH2:13]/[CH:14]=[C:15](\[CH3:22])/[CH2:16][CH2:17][C:18]([O:20]C)=[O:19])=[C:11]([O:23][CH3:24])[C:10]([CH3:25])=[C:9]2[C:5]=1[C:6](=[O:26])[O:7][CH2:8]2)=C=O.O.O.[OH-].[Li+].C(OCC)(=O)C>O1CCOCC1.C(O)(=O)C>[NH2:1][C:4]1[C:12]([CH2:13]/[CH:14]=[C:15](\[CH3:22])/[CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[C:11]([O:23][CH3:24])[C:10]([CH3:25])=[C:9]2[C:5]=1[C:6](=[O:26])[O:7][CH2:8]2

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 15229925HCID 15229925, compound

Product 1

HCID 9948928HCID 9948928, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

9.0 g (5.5 mmol) of methyl (B)-6-(4-carboxy-1,3-dihydro-6-methoxy-7methyl-3-oxoisobenzofuran-5-yl)-4-methyl -4-hexenoate, a compound of Formula 5, was converted to crude methyl E-6-(1,3-dihydro-4-isocyanato-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate, a compound of Formula 6, as described in Preparation 6 above without purification. The resulting 4-isocyanate was redissolved in 50 ml of 1,4-dioxane and treated with 16 ml of water and 2.0 g (47.7 mmol) of lithium hydroxide monohydrate. The mixture was stirred at room temperature for 2 hours and then partitioned between aqueous 1N sodium hydrogen sulfate and ethyl acetate. The organic phase was washed twice with water, once with brine, and was dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by chromatography on silica gel, using 50:40:1 hexane:ethyl acetate:acetic acid as eluant to give 1.28 g (4.0 mmol) of (E)-6-(4-amino-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic acid as a white solid, mp 130°-131° C.

Workup

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

Sources & evidence

ORD record
ord-1ea20f5ab2014ec38c47da6903af962b
Source dataset
uspto-grants-1996_07
Patent number
US05538969

Reaction notes

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