Tetrahydrofuran → 4-Amino-2-benzoyl-2'-methoxymethoxy-6'-methoxy-biphenyl

HRID 1358115Notes

Reaction equation

HRID 1358115 reaction equation
CON(C)[C:4]([C:6]1[C:7]([C:13]2[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=2[O:21][CH2:22]OC)=[CH:8][CH:9]=[C:10]([NH2:12])[CH:11]=1)=[O:5].[C:26]1([Li])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1C[O:36][CH2:35]C1>>[NH2:12][C:10]1[CH:9]=[CH:8][C:7]([C:13]2[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=2[O:21][CH2:22][O:36][CH3:35])=[C:6]([C:4](=[O:5])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:11]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 18189391n-Methoxy-n-methyl-4-amino-2'-methoxymethoxy-6'methoxy-biphenyl-2-carboxamideHCID 178506676HCID 178506676, compound

Product 1

HCID 181885574-Amino-2-benzoyl-2'-methoxymethoxy-6'-methoxy-biphenylYield 85%

Conditions

Temperature
-5 °C

Procedure

A solution of Example 5C (5.44 g., 15.72 mmole) in THF (70 mL) and cooled to −5° C. was treated with of 1.8M phenyllithium in ether-cyclohexane (52.4 mL, 94.33 mmol). The mixture was stirred at −5° C. for 1 hour, cooled to −78° and a solution of aqueous KHCO3 was added rapidly. The mixture was extracted with ether, which was combined, dried (Na2SO4), filtered, concentrated under reduced pressure and purified on silica gel eluting with 8% ethyl acetate in CH2Cl2 to provide the titled compound (4.84 g, 85% yield).

Workup

  1. temperaturecooled to −78°
  2. extractionThe mixture was extracted with ether, which
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. custompurified on silica gel eluting with 8% ethyl acetate in CH2Cl2

Sources & evidence

ORD record
ord-0879ccf71e0c4ecc8e3bbbe7d4d4507b
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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