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

HRID 660377노트

반응식

HRID 660377 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

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온도
20 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-1f6ca04dc6b04280a1dd861f6be076d9
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084485B2

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