Succinic anhydride → HCID 52920221, compound

HRID 547850Notes

Reaction equation

HRID 547850 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[CH:18]=2)=[CH:11][CH:10]=1.[C:26]1(=[O:32])[O:31][C:29](=[O:30])[CH2:28][CH2:27]1>C1COCC1.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:18]=[C:19]([NH:23][C:26](=[O:32])[CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH:20]=[CH:21][CH:22]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 7922Succinic anhydrideHCID 582877952,4-Difluoro-4'-(3-nitro-benzyloxy)-biphenyl

Product 1

HCID 52920221HCID 52920221, compoundYield 20.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,4-difluoro-4′-(3-nitro-benzyloxy)-biphenyl (28 mg, 0.082 mmol), succinic anhydride (8.2 mg, 0.083 mmol) and 10% Pd/C (4.4 mg) in THF (3 mL) was hydrogenated at 45 psi for 4 hrs. The reaction mixture was filtered and evaporated. The crude product was purified by flash chromatography with a 0-50% gradient of ethyl acetate in hexanes to yield 7 mg (20.7%) of N-[3-(2′,4′-difluoro-biphenyl-4-yloxymethyl)-phenyl]-succinamic acid as a solid. LC-MS (ES) calculated for C23H19F2NO4, 411.41; found m/z 410.2 [M−H]−.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. customThe crude product was purified by flash chromatography with a 0-50% gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-3f060642cbde41e0839ed17e7824fad1
Source dataset
uspto-grants-2011_05
Patent number
US07939569B1

Reaction notes

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