HCID 25152049, compound → HCID 68409918, compound

HRID 2066824Notes

Reaction equation

HRID 2066824 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:38]([CH3:40])[CH3:39])[C:6]2[O:10][C:9]([C:11]3[CH:36]=[CH:35][C:14]([C:15]([NH:17][CH2:18][C:19]4([CH3:34])[O:23][C:22](=[O:24])[N:21](CC5C=CC(OC)=CC=5)[CH2:20]4)=[O:16])=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:37]=1)#[N:2]>C(#N)C.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:38]([CH3:40])[CH3:39])[C:6]2[O:10][C:9]([C:11]3[CH:36]=[CH:35][C:14]([C:15]([NH:17][CH2:18][C:19]4([CH3:34])[O:23][C:22](=[O:24])[NH:21][CH2:20]4)=[O:16])=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:37]=1)#[N:2]

Participants

4

Reactant 1

HCID 25152049HCID 25152049, compound

Product 1

HCID 68409918HCID 68409918, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-{[3-(4-methoxybenzyl)-5-methyl-2-oxo-1,3-oxazolidin-5-yl]methyl}benzamide (598 mg, EXAMPLE 65) in 18.0 ml of acetonitrile and 6.0 ml of water was added 1.52 g of ceric ammonium nitrate. The mixture was stirred at room temperature for 15 h, and then concentrated in vacuo. The residue was dissolved in 10 ml of dichloromethane and purified via column chromatography on a Biotage Horizon 65i column eluting with 0% ethyl acetate in hexanes (1 column volume), followed by a gradient to 100% ethyl acetate in hexanes (over 10 column volumes), and held at 100% ethyl acetate for 2 column volumes to remove all the impurities. The column was then flushed with methanol (5 column volumes) to provide the title compound (242 mg, 52%) as a white solid. Mass spectrum (ESI) 419.1 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in 10 ml of dichloromethane
  3. custompurified via column chromatography on a Biotage Horizon 65i column
  4. washeluting with 0% ethyl acetate in hexanes (1 column volume)
  5. customto remove all the impurities
  6. customThe column was then flushed with methanol (5 column volumes)

Sources & evidence

ORD record
ord-4d73246066cb42389ff196a08015192f
Source dataset
uspto-grants-2012_10
Patent number
US08293721B2

Reaction notes

Loading…