Potassium Persulfate → (4R,5S)-Methyl 5-(4-(2-methoxyethoxy)phenyl)-2-oxooxazolidine-4-carboxylate

HRID 929947노트

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HRID 929947 반응식
C([O:5][C:6]([NH:8][C@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])(C)(C)C.S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+]>C(#N)C.O.[O-]S([O-])(=O)=O.[Cu+2]>[CH3:13][O:12][CH2:10][CH2:9][O:21][C:18]1[CH:17]=[CH:16][C:15]([C@@H:14]2[O:7][C:6](=[O:5])[NH:8][C@H:9]2[C:10]([O:12][CH3:13])=[O:11])=[CH:20][CH:19]=1

참가 물질

6

반응물 2

HCID 24412Potassium PersulfateHCID 7016055Boc-D-Tyr-OMe

생성물 1

HCID 86718529(4R,5S)-Methyl 5-(4-(2-methoxyethoxy)phenyl)-2-oxooxazolidine-4-carboxylate수율 110%

시약·촉매·용매 3

HCID 24462Copper Sulfate촉매HCID 962Water용매2회HCID 6342Acetonitrile용매

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온도
70 °C

실험 절차

To a solution of (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)-propanoate (5.34 g, 14.35 mmol) in acetonitrile (260 mL) was added under argon a solution of potassium persulfate (7.76 g, 28.7 mmol) in H2O (190 mL) and a solution of CuSO4 (0.458 g, 2.87 mmol) dissolved in H2O (70 mL). The resulting mixture was stirred for 3 h at 70° C. The reaction mixture was extracted with EtOAc. Combined extracts were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using EtOAc in heptane from 20% to 100% in order to give the title compound as a yellow oil (2.33 g, 52%). TLC (heptane/EtOAc 1:2) Rf=0.19; tR=0.680 min (UPLC 1); LC-MS: [M+H] 296; Rt 0.68 min; (LCMS method 2); 1H NMR (400 MHz, CDCl3): 7.36 (d, 2H), 6.99 (d, 2H), 5.86 (br d, 1H), 5.62 (d, 1H), 4.30 (d, 1H), 4.16 (dd, 2H), 3.88 (s, 3H), 3.79 (dd, 2H), 3.48 (s, 3H).

후처리

  1. extractionThe reaction mixture was extracted with EtOAc
  2. washCombined extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-5c0eac984ba348acb9f861f0eacf8e4d
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296733B2

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