Ethyl Acetate → HCID 69285681, compound

HRID 2225305Notes

Reaction equation

HRID 2225305 reaction equation
[OH:1][CH:2]([CH:32]([CH3:34])[CH3:33])[CH2:3][C@@H:4]1[CH2:9][C@H:8]([N:10]([CH:12]([CH3:14])[CH3:13])[CH3:11])[CH2:7][CH2:6][C@@H:5]1[NH:15][C:16](=[O:31])[CH2:17][NH:18][C:19](=[O:30])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.CCOC(C)=O>C(Cl)Cl>[CH:12]([N:10]([CH3:11])[C@@H:8]1[CH2:7][CH2:6][C@H:5]([NH:15][C:16](=[O:31])[CH2:17][NH:18][C:19](=[O:30])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[CH:21]=2)[C@H:4]([CH2:3][C:2](=[O:1])[CH:32]([CH3:34])[CH3:33])[CH2:9]1)([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724130Cornforth reagentHCID 69286678HCID 69286678, compound

Product 1

HCID 69285681HCID 69285681, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the isomeric mixture of N-(2-((1S,2S,4R)-2-(2-hydroxy-3-methylbutyl)-4-(isopropyl(methyl)amino)cyclohexylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide (34 mg; see Examples 11p and 11q) in 3 ml of anhydrous CH2Cl2 were added excess amounts of powdered 4A molecular sieves and pyridinium dichromate, and the mixture was stirred for 2 hours at room temperature. After addition of about 15 ml of EtOAc it was filtered through a plug of Celite, and evaporated to give an oily residue, which was purified by chromatography (silica gel, CH2Cl2 then 1:9:90 cNH4OH-MeOH—CH2Cl2) to give N-(2-((1S,2S,4R)-4-(isopropyl(methyl)amino)-2-(3-methyl-2-oxobutyl)cyclohexylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide as an amorphous solid. MS found: (M+H)+=484.3.

Workup

  1. additionwere added excess amounts
  2. filtrationwas filtered through a plug of Celite
  3. customevaporated
  4. customto give an oily residue, which
  5. customwas purified by chromatography (silica gel, CH2Cl2

Sources & evidence

ORD record
ord-38cc83708bb346869deef7c5c61a5a0d
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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