Phosphate → N-[3-({2-[(6-{[(2R)-2-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]ethoxy}methyl)phenyl]-N'-phenylurea

HRID 1014804Notes

Reaction equation

HRID 1014804 reaction equation
C[Si](C)(C)[O-].[K+].[CH3:7][C:8]1([CH3:51])[O:13][C:12]2[CH:14]=[CH:15][C:16]([C@H:18]3[O:22]C(=O)[N:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][C:35]4[CH:36]=[C:37]([NH:41][C:42]([NH:44][C:45]5[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=5)=[O:43])[CH:38]=[CH:39][CH:40]=4)[CH2:19]3)=[CH:17][C:11]=2[CH2:10][O:9]1.P([O-])([O-])([O-])=O>C1COCC1>[CH3:7][C:8]1([CH3:51])[O:13][C:12]2[CH:14]=[CH:15][C:16]([C@@H:18]([OH:22])[CH2:19][NH:20][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][C:35]3[CH:36]=[C:37]([NH:41][C:42]([NH:44][C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)=[O:43])[CH:38]=[CH:39][CH:40]=3)=[CH:17][C:11]=2[CH2:10][O:9]1

Participants

5

Reactant 3

HCID 1061PhosphateHCID 23668039Potassium trimethylsilanolate2×HCID 66845296N-(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)-N'-phenylurea

Product 1

HCID 66845022N-[3-({2-[(6-{[(2R)-2-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]ethoxy}methyl)phenyl]-N'-phenylureaYield 46.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Potassium trimethylsilanolate (0.056 g) was added to a solution of N-(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)-N′-phenylurea (0.061 g) in degassed anhydrous THF (4 ml) whilst stirring under nitrogen. The reaction mixture was heated to 65° C. for 4 h, adding additional potassium trimethylsilanolate (0.057 g) and heated for a further 2.5 h, at which point the reaction mixture was cooled to room temperature. Phosphate buffer (20 ml, pH6.5) was added and the mixture extracted with EtOAc (3×20 ml). The combined organic layers were separated and dried over Na2SO4 before filtering. Solvent evaporation in vacuo gave the title compound (0.027 g). LCMS RT=2.80 min, ES+ve 592 (MH)+.

Workup

  1. temperatureheated for a further 2.5 h, at which
  2. temperaturewas cooled to room temperature
  3. extractionthe mixture extracted with EtOAc (3×20 ml)
  4. customThe combined organic layers were separated
  5. dry with materialdried over Na2SO4
  6. filtrationbefore filtering
  7. customSolvent evaporation in vacuo

Sources & evidence

ORD record
ord-97ef48e1a79a48f3993adf03e2f92a23
Source dataset
uspto-grants-2011_07
Patent number
US07982067B2

Reaction notes

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