HCID 66697283, compound → HCID 66697171, compound

HRID 2096791Notes

Reaction equation

HRID 2096791 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:38])[C:18]([C:24]3[CH:25]=[CH:26][C:27]4[O:32][CH2:31][C:30](=[O:33])[N:29](CC=C)[C:28]=4[CH:37]=3)([OH:23])[C:19]([F:22])([F:21])[F:20])=[C:13]([Cl:39])[CH:12]=2)=[CH:7][C:6]=1[F:40])=[O:4]>C(O)CC.[Rh](Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:38])[C:18]([OH:23])([C:24]3[CH:25]=[CH:26][C:27]4[O:32][CH2:31][C:30](=[O:33])[NH:29][C:28]=4[CH:37]=3)[C:19]([F:22])([F:21])[F:20])=[C:13]([Cl:39])[CH:12]=2)=[CH:7][C:6]=1[F:40])=[O:4]

Participants

4

Reactant 1

HCID 66697283HCID 66697283, compound

Product 1

HCID 66697171HCID 66697171, compoundYield 28.7%

Reagents, catalysts & solvents 2

HCID 24872Rhodium chlorideCatalystHCID 10311-PropanolSolvent

Procedure

To a suspension of 3′-chloro-3-fluoro-4′-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-propyl]-biphenyl-4-carboxylic acid methyl ester (255 mg, 0.44 mmol, Example 70, step 7) in n-propanol (5 ml) was added rhodium(III)chloride (10 mg, 0.04 mmol). The mixture was stirred under reflux for 18 h. The reaction mixture was concentrated. The crude product was purified by flash chromatography (silica gel, heptane/AcOEt 8:2=>7:3) to give the title compound (68 mg) as a white solid. MS (m/e)=538.3 [M+H+].

Workup

  1. temperatureunder reflux for 18 h
  2. concentrationThe reaction mixture was concentrated
  3. customThe crude product was purified by flash chromatography (silica gel, heptane/AcOEt 8:2=>7:3)

Sources & evidence

ORD record
ord-b287569f5e70402290ad62f1cbf65292
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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