Triethylamine → HCID 10157949, compound

HRID 584903Notes

Reaction equation

HRID 584903 reaction equation
[CH3:1][N:2]([CH2:11][C:12]1[CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26](Cl)=[O:27])=[CH:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C([Si](C)(C)[O:34][NH2:35])(C)(C)C.[CH2:38](N(CC)CC)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:34][NH:35][C:26]([CH:25]([CH3:38])[CH2:24][C:21]1[CH:22]=[CH:23][C:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([CH2:11][N:2]([CH3:1])[C:3](=[O:4])[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:13]=2)=[CH:19][CH:20]=1)=[O:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 4691350O-(tert-Butyldimethylsilyl)hydroxylamineHCID 22341459HCID 22341459, compound

Product 1

HCID 10157949HCID 10157949, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By reacting a solution of 669 mg (1.65 mmol) of 3-(3′-{[methyl-(1-phenylmethanoyl)amino]-methyl}biphenyl-4-yl)propionyl chloride in 6 ml of THF with 243 mg (1.65 mmol) of O-(tert-butyldimethyl-silyl) hydroxylamine in the presence of 250 μl (1.8 mmol) of triethylamine, followed by deprotection with 530 μl of tetrabutylammonium fluoride solution (1N in THF), and after purification by chromatography on a column of silica, 350 mg (42%) of N-[4′-(2-hydroxy-carbamoylpropyl)biphenyl-3-ylmethyl]-N-methylbenzamide, with a melting point of 65-66° C., are obtained.

Workup

  1. customafter purification by chromatography on a column of silica, 350 mg (42%) of N-[4′-(2-hydroxy-carbamoylpropyl)biphenyl-3-ylmethyl]-N-methylbenzamide
  2. customwith a melting point of 65-66° C., are obtained

Sources & evidence

ORD record
ord-ed063ce24adc43c0852c8dbacd1ad509
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

Loading…