HCID 131726587, compound → HCID 131726586, compound

HRID 915713Notes

Reaction equation

HRID 915713 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[C:29]([C:31]([O:33]C)=[O:32])[C:28]([N+:35]([O-:37])=[O:36])=[CH:27][C:4]=1[O:5][C:6]([O:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[C:15]([C:21]([O:23]C)=[O:22])=[CH:14][C:13]=1[O:25][CH3:26])([CH2:9][CH3:10])[CH2:7][CH3:8]>[OH-].[Na+].C1COCC1>[C:21]([C:15]1[C:16]([N+:18]([O-:20])=[O:19])=[CH:17][C:12]([O:11][C:6]([O:5][C:4]2[CH:27]=[C:28]([N+:35]([O-:37])=[O:36])[C:29]([C:31]([OH:33])=[O:32])=[CH:30][C:3]=2[O:2][CH3:1])([CH2:9][CH3:10])[CH2:7][CH3:8])=[C:13]([O:25][CH3:26])[CH:14]=1)([OH:23])=[O:22]

Participants

4

Reactant 1

HCID 131726587HCID 131726587, compound

Product 1

HCID 131726586HCID 131726586, compoundYield 104.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of the ester 52 (9.0 g, 17.2 mmol) in aqueous sodium hydroxide (1 M, 180 mL) and THF (180 mL) was allowed to stir until a homogenous solution was obtained (2 days). THF was evaporated under reduced pressure and the resulting aqueous suspension was filtered to remove any unreacted starting material. The filtrate was adjusted to pH 1, the precipitated product was collected by filtration and air dried to afford the desired bis-acid (53) (8.88 g). A higher than theoretical yield was obtained due to the inclusion of the sodium salt of acid. The salt may be removed by dissolving the bulk of the material in THF and removing the insoluble material by filtration: 1H NMR (400 MHz, CDCl3) δ 7.39 (s, 2H), 7.16 (s, 2H), 4.12 (t, 4H, J=6.59 Hz), 3.95 (s, 6H), 2.00-1.85 (m, 4H), 1.75-1.67 (m, 2H).

Workup

  1. customwas obtained (2 days)
  2. customTHF was evaporated under reduced pressure
  3. filtrationthe resulting aqueous suspension was filtered
  4. customto remove
  5. filtrationthe precipitated product was collected by filtration and air
  6. customdried

Sources & evidence

ORD record
ord-7a014add5814413cad53785efa5662a3
Source dataset
uspto-grants-2007_09
Patent number
US07265105B2

Reaction notes

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