Phosphate → (5R)-3-(6-{2-[(4-aminobenzyl)oxy]ethoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 219047Notes

Reaction equation

HRID 219047 reaction equation
[CH3:1][C:2]1([CH3:49])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[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:34]=[CH:33][C:32]([N:35]=C(C5C=CC=CC=5)C5C=CC=CC=5)=[CH:31][CH:30]=4)[CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.C([O-])(=O)C.[Na+].Cl.NO.P([O-])([O-])([O-])=O>CO>[NH2:35][C:32]1[CH:31]=[CH:30][C:29]([CH2:28][O:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][N:14]2[CH2:13][C@@H:12]([C:10]3[CH:9]=[CH:8][C:6]4[O:7][C:2]([CH3:1])([CH3:49])[O:3][CH2:4][C:5]=4[CH:11]=3)[O:16][C:15]2=[O:17])=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 1061PhosphateHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86597512(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[2-({4-[(diphenylmethylene)amino]benzyl}oxy)ethoxy]hexyl}-1,3-oxazolidin-2-one

Product 1

HCID 66845317(5R)-3-(6-{2-[(4-aminobenzyl)oxy]ethoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneYield 49.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[2-({4-[(diphenylmethylene)amino]benzyl}oxy)ethoxy]hexyl}-1,3-oxazolidin-2-one (860 mg) in MeOH (13 ml) was treated with sodium acetate (255 mg) followed by hydroxylamine hydrochloride (162 mg) and the mixture was stirred at 20° for 0.5 h. Phosphate buffer solution (30 ml, pH6.5) was added and the mixture was extracted with EtOAc. The combined extracts were dried (Na2SO4) and the solvent evaporated in vacuo. The residue was purified by SPE (silica, 10 g). Elution with EtOAc-cyclohexane (1:1) then (4:1) gave the title compound (321 mg). LCMS RT=3.18 min.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. customthe solvent evaporated in vacuo
  4. customThe residue was purified by SPE (silica, 10 g)
  5. washElution with EtOAc-cyclohexane (1:1)

Sources & evidence

ORD record
ord-34faa6be1dc44ee7a6c677e074312865
Source dataset
uspto-grants-2012_06
Patent number
US08198483B2

Reaction notes

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