Pyridine → Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({2'-[(hydroxyimino)methyl]-4'-[(methoxycarbonyl)methyl]-1,1'-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate

HRID 2076658Notes

Reaction equation

HRID 2076658 reaction equation
N1C=CC=CC=1.Cl.[NH2:8][OH:9].[C:10]([O:14][C:15]([O:17][C:18]1[C:30]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:28]=[C:27]([CH2:35][O:36][C:37]2[CH:42]=[CH:41][C:40]([C:43]3[CH:48]=[CH:47][C:46]([CH2:49][C:50]([O:52][CH3:53])=[O:51])=[CH:45][C:44]=3[CH:54]=O)=[CH:39][CH:38]=2)[C:19]=1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:16])([CH3:13])([CH3:12])[CH3:11]>C(O)C.C(OCC)(=O)C>[C:10]([O:14][C:15]([O:17][C:18]1[C:30]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:28]=[C:27]([CH2:35][O:36][C:37]2[CH:42]=[CH:41][C:40]([C:43]3[CH:48]=[CH:47][C:46]([CH2:49][C:50]([O:52][CH3:53])=[O:51])=[CH:45][C:44]=3[CH:54]=[N:8][OH:9])=[CH:39][CH:38]=2)[C:19]=1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 86617414Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({2'-formyl-4'-[(methoxycarbonyl)methyl]-1,1'-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate

Product 1

HCID 86617415Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({2'-[(hydroxyimino)methyl]-4'-[(methoxycarbonyl)methyl]-1,1'-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoateYield 83.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyridine (49 μl, 0.62 mmol) and hydroxylamine hydrochloride (42 mg, 0.62 mmol) were added to a solution of tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({2′-formyl-4′-[(methoxycarbonyl)methyl]-1,1′-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate (198 mg, 0.307 mmol) obtained in Example (45-2) in ethanol (4 ml), and the mixture was stirred at room temperature for 4 hours. The reaction mixture was diluted with ethyl acetate, successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was subjected to silica gel preparative thin layer chromatography (developing solvent: n-hexane/ethyl acetate=2/1) to give crude tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({2′-[(hydroxyimino)methyl]-4′-[(methoxycarbonyl)methyl]-1,1′-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate (170 mg).

Workup

  1. washsuccessively washed with water
  2. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  3. customThe residue obtained
  4. customby removing the solvent under reduced pressure

Sources & evidence

ORD record
ord-aea64be630d74e6b88969e2ee64ef94a
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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