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 219047ノート

反応式

HRID 219047 の反応式
[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

参加物

6

反応物 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

生成物 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-one収率 49.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-34faa6be1dc44ee7a6c677e074312865
出典データセット
uspto-grants-2012_06
特許番号
US08198483B2

反応ノート

読み込み中…