Phosphate → N-(3-{[({3-[(2-[(6-({(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy}ethoxy)methyl]phenyl}amino)carbonyl]amino)-phenyl)pyridine-3-carboxamide

HRID 219025Notes

Reaction equation

HRID 219025 reaction equation
[CH3:1][C:2]1([CH3:54])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16]C(=O)[N:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][C:29]4[CH:30]=[C:31]([NH:35][C:36]([NH:38][C:39]5[CH:40]=[C:41]([NH:45][C:46]([C:48]6[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=6)=[O:47])[CH:42]=[CH:43][CH:44]=5)=[O:37])[CH:32]=[CH:33][CH:34]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.C[Si](C)(C)[O-].[K+].P([O-])([O-])([O-])=O>C1COCC1>[CH3:1][C:2]1([CH3:54])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@@H:12]([OH:16])[CH2:13][NH:14][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][C:29]3[CH:30]=[C:31]([NH:35][C:36]([NH:38][C:39]4[CH:40]=[C:41]([NH:45][C:46]([C:48]5[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=5)=[O:47])[CH:42]=[CH:43][CH:44]=4)=[O:37])[CH:32]=[CH:33][CH:34]=3)=[CH:11][C:5]=2[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 1061PhosphateHCID 23668039Potassium trimethylsilanolateHCID 66845055N-{3-[({[3-({2-({6-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy}methyl)phenyl]amino}carbonyl)amino]-phenyl}pyridine-3-carboxamide

Product 1

HCID 66844859N-(3-{[({3-[(2-[(6-({(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy}ethoxy)methyl]phenyl}amino)carbonyl]amino)-phenyl)pyridine-3-carboxamideYield 54.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-{3-[({[3-({2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy}methyl)phenyl]amino}carbonyl)-amino]phenyl}pyridine-3-carboxamide (0.209 g) in anhydrous THF (10 ml) was treated under nitrogen at 20° with potassium trimethylsilanolate (0.217 g). The mixture was heated to 65° for 2.5 h before cooling to room temperature. Phosphate buffer (pH 6.5, 25 ml) was added and the product extracted with EtOAc (3×20 ml). Solvent evaporation in vacuo gave a residue that was purified by SPE. Elution with dichloromethane-EtOH-ammonia (100:8:1 then 50:8:1) followed by solvent evaporation in vacuo gave the title compound (0.109 g). LCMS RT=2.86 min, ES+ve 712 (MH)+.

Workup

  1. temperatureThe mixture was heated to 65° for 2.5 h
  2. extractionthe product extracted with EtOAc (3×20 ml)
  3. customSolvent evaporation in vacuo
  4. customgave a residue that
  5. customwas purified by SPE
  6. washElution with dichloromethane-EtOH-ammonia (100:8:1
  7. custom50:8:1) followed by solvent evaporation in vacuo

Sources & evidence

ORD record
ord-f72805aed28f497f8b495bc00575d2dc
Source dataset
uspto-grants-2012_06
Patent number
US08198483B2

Reaction notes

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