Hydrogen Peroxide → (S)-2-(benzyloxymethyl)-3-methylbutanoic acid

HRID 660377ノート

反応式

HRID 660377 の反応式
C([C@@H]1COC(=O)N1[C:14](=[O:28])[C@H:15]([CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:16]([CH3:18])[CH3:17])C1C=CC=CC=1.OO.[Li+].[OH-].[O-:33]S([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C1COCC1.O>[CH2:21]([O:20][CH2:19][C@H:15]([CH:16]([CH3:17])[CH3:18])[C:14]([OH:28])=[O:33])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参加物

7

反応物 5

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 46741251(4R)-3-[(2S)-3-Methyl-1-oxo-2-[(phenylmethoxy)methyl]butyl]-4-(phenylmethyl)-2-oxazolidinone

生成物 1

HCID 11492274(S)-2-(benzyloxymethyl)-3-methylbutanoic acid収率 82%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

反応条件

温度
20 °C

実験手順

To a solution of (R)-4-benzyl-3-((S)-2-(benzyloxymethyl)-3-methylbutanoyl)oxazolidin-2-one (127 g, 0.33 mol) in 3:1 THF/H2O (2 L), cooled in an ice bath, were added 30% aq H2O2 (235 mL, 2.07 mol) and LiOH (28 g, 0.66 mol). The mixture was stirred at 20° C. for 3 h, followed by cooling to 0° C. Then 1.5 M aq Na2SO3 (1.38 L, 3.83 mol) was added dropwise within 30 min. After addition of satd aq NaHCO3 (500 mL), volatiles were evaporated, and the aqueous phase was washed with Et2O (3×600 mL). The organic layers were discarded. The aqueous layer was adjusted to pH 3 by adding 2 N aq HCl and extracted with CH2 Cl2 (3×800 mL). The combined organic layers were washed with satd aq NaCl (1 L), dried over Na2SO4, and evaporated to give (S)-2-(benzyloxymethyl)-3-methylbutanoic acid (60 g, 82%). 1H NMR (400 MHz, CDCl3): 0.98 (m, 6H), 2.01 (m, 1H), 2.53 (m, 1H), 3.67 (m, 2H), 4.55 (s, 2H), 7.30 (m, 6H)

後処理

  1. temperatureby cooling to 0° C
  2. customwere evaporated
  3. washthe aqueous phase was washed with Et2O (3×600 mL)
  4. additionby adding 2 N aq HCl
  5. extractionextracted with CH2 Cl2 (3×800 mL)
  6. washThe combined organic layers were washed with satd aq NaCl (1 L)
  7. dry with materialdried over Na2SO4
  8. customevaporated

出典と根拠

ORDレコード
ord-1f6ca04dc6b04280a1dd861f6be076d9
出典データセット
uspto-grants-2011_12
特許番号
US08084485B2

反応ノート

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