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

HRID 929947ノート

反応式

HRID 929947 の反応式
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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24462Copper Sulfate触媒HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5c0eac984ba348acb9f861f0eacf8e4d
出典データセット
uspto-grants-2016_03
特許番号
US09296733B2

反応ノート

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