(5S)-2-(4-bromophenyl)-5-isobutyl-1,3-dioxolan-4-one → (2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-4-methylpentanoic acid

HRID 1180370노트

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HRID 1180370 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12][C:11](=[O:13])[C@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[O:9]2)=[CH:4][CH:3]=1.[C:18]1([Mg]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOCC.[Cl-].[Zn+2].[Cl-]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:9][C@@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]([OH:12])=[O:13])=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 69473106(5S)-2-(4-bromophenyl)-5-isobutyl-1,3-dioxolan-4-oneHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 69470808(2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-4-methylpentanoic acid

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 3283Diethyl Ether용매3회

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온도
0 °C

실험 절차

Zinc chloride (1.12 l of 1M solution in ether, 1120 mmol) was added to 500 ml ether at −40° C. (5S)-2-(4-bromophenyl)-5-isobutyl-1,3-dioxolan-4-one (3:2 mixture of cis/trans) (56 g, 187 mmol) was then added dropwise in 200 ml ether (over 15 min), followed by phenylmagnesium bromide (125 ml of a 3M solution in ether, 374 mmol) (dropwise over 45 min). The solution was stirred at 0° C. for 2 hours. The reaction was quenched at 0° C. with 800 ml of a saturated solution of NH4Cl, the phases were separated and the aqueous layer extracted with 800 ml ether. The organic layers were combined, washed with brine, dried with MgSO4 and the solvent was removed. (2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-4-methylpentanoic acid (de=86%) was obtained after purification on silica gel (5% ethyl acetate/toluene).

후처리

  1. customdropwise over 45 min
  2. customThe reaction was quenched at 0° C. with 800 ml of a saturated solution of NH4Cl
  3. customthe phases were separated
  4. extractionthe aqueous layer extracted with 800 ml ether
  5. washwashed with brine
  6. dry with materialdried with MgSO4
  7. customthe solvent was removed

출처 및 근거

ORD 기록
ord-34803b8b41f64fb8884fe156d307df9c
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279478B2

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