Ethyl Acetate → 1-(2-(2-((5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenylamino)methyl)-1-trityl-1H-imidazol-4-yl)phenyl)propan-1-one

HRID 2104985Notes

Reaction equation

HRID 2104985 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:59][CH:60]([CH3:62])[CH3:61])[C:7]([F:58])=[C:8]([CH:10]([NH:45][C:46]2[CH:51]=[CH:50][C:49]([C:52]3[N:56]=[C:55]([CH3:57])[O:54][N:53]=3)=[CH:48][CH:47]=2)[C:11]2[N:12]([C:26]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH:22]([OH:25])[CH2:23][CH3:24])[N:15]=2)[CH:9]=1)[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOC(C)=O.[OH-].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:59][CH:60]([CH3:62])[CH3:61])[C:7]([F:58])=[C:8]([CH:10]([NH:45][C:46]2[CH:51]=[CH:50][C:49]([C:52]3[N:56]=[C:55]([CH3:57])[O:54][N:53]=3)=[CH:48][CH:47]=2)[C:11]2[N:12]([C:26]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22](=[O:25])[CH2:23][CH3:24])[N:15]=2)[CH:9]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 688125741-(2-(2-((5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenylamino)methyl)-1-trityl-1H-imidazol-4-yl)phenyl)propan-1-ol

Product 1

HCID 688132671-(2-(2-((5-ethoxy-2-fluoro-3-isopropoxyphenyl)(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenylamino)methyl)-1-trityl-1H-imidazol-4-yl)phenyl)propan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Intermediate 122.2 and Dess-Martin periodinate (60 mg, 0.12 mmol) in anhydrous CH2Cl2 (2 mL) was stirred at rt for 20 min. The reaction mixture was then partionated between EtOAc and 1 N NaOH, the organic layer was collected and dried over (Na2SO4), filtered and concentrated to afford Intermediate 122.3, which was used in the following step without further purification. LCMS (2 min gradient) RT=2.27 min, 826.4 (M+H).

Workup

  1. customthe organic layer was collected
  2. dry with materialdried over (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fc281341685d4b629e7dc58c371263d1
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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