HCID 86619841, compound → HCID 11689795, compound

HRID 1994303Notes

Reaction equation

HRID 1994303 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:10]([CH:21]([CH:33]([CH3:35])[CH3:34])[C:22]([NH:24][O:25]CC2C=CC=CC=2)=[O:23])[C:9]1=[O:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].[O-]S([O-])(=O)=O.[Ba+2].CO>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:10]([CH:21]([CH:33]([CH3:34])[CH3:35])[C:22]([NH:24][OH:25])=[O:23])[C:9]1=[O:36])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86619841HCID 86619841, compound

Product 1

HCID 11689795HCID 11689795, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolvent

Procedure

2-(3-Benzyl-5-(4-methoxyphenyl)-2-oxoimidazolidin-1-yl)-N-benzyloxy-3-methylbutyramide (120 mg; 0.24 mmol) was introduced into methanol (10 ml), and Pd/BaSO4 (50 mg) was added. The mixture was hydrogenated with H2 (1 atm) at RT for 4 h. The reaction mixture was then filtered through kieselguhr, the residue was washed with methanol, and the filtrate was concentrated in a rotary evaporator. Purification by preparative HPLC resulted in 2-(3-benzyl-5-(4-methoxyphenyl)-2-oxoimidazolidin-1-yl)-N-hydroxy-3-methylbutyramide (60 mg, 0.15 mmol). MS: 398.15 (M+H); Rt: 1.31 min (method: gradient 0 min 96% H2O (0.05% TFA) 2.0 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 4% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was then filtered through kieselguhr
  3. washthe residue was washed with methanol
  4. concentrationthe filtrate was concentrated in a rotary evaporator
  5. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-7bd1d150d4154e2a8d93f0724ec8b0e0
Source dataset
uspto-grants-2010_01
Patent number
US07652143B2

Reaction notes

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