Dichloromethane → HCID 66827699, compound

HRID 1037752Notes

Reaction equation

HRID 1037752 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:33])[C:10]([NH:12][NH:13][C:14](=[O:32])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:17]([CH3:29])[C:16]=2[CH2:30][CH3:31])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.ClCCl.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:33])[C:10]([NH:12][NH:13][C:14](=[O:32])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[C:17]([CH3:29])[C:16]=2[CH2:30][CH3:31])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 66827697HCID 66827697, compound

Product 1

HCID 66827699HCID 66827699, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

172 mg of N′-[2-(3,5-difluorophenyl)-2-hydroxyacetyl]-4-benzyloxy-2-ethyl-3-methylbenzohydrazide (C3) are dissolved in 0.9 ml of dimethyl sulfoxide and 28 ml of dichloromethane under a dry nitrogen atmosphere. 185 mg of triacetoxyperiodinane (Dens-Martin reagent) are subsequently added. The suspension is stirred at room temperature for 1 h. For work-up, 100 ml of dichloromethane and 30 ml of 0.5 M Na2S2O3 solution are added. The organic phase is subsequently extracted with 50 ml of sat. NaHCO3 solution, dried over Na2SO4, filtered off with suction and evaporated to dryness. The residue is purified by means of flash column chromatography on silica gel (solvent gradient: cyclohexane/0-30% by vol. of methyl tert-butyl ether), giving 163 mg of the title compound as amorphous solid; MS: 452.7 (2M+H+); TLC: Rf=0.37 (cyclohexane/ethyl acetate 2:1, parts by volume).

Workup

  1. extractionThe organic phase is subsequently extracted with 50 ml of sat. NaHCO3 solution
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered off with suction
  4. customevaporated to dryness
  5. customThe residue is purified by means of flash column chromatography on silica gel (solvent gradient: cyclohexane/0-30% by vol. of methyl tert-butyl ether)

Sources & evidence

ORD record
ord-88a0321bcdea48bcb2a3a20efb9257a8
Source dataset
uspto-grants-2013_10
Patent number
US08546613B2

Reaction notes

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