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HRID572654

反应详情

EQUATION

反应方程式

HRID 572654 的结构方程式

REACTANTS

反应物

3
结构：CC(=O)O.CC(=O)O.Ic1ccccc1
HCID12217721

未命名化合物

结构：C=C[C@H]1CO[C@H](COS(=O)(=O)c2ccc(C)cc2)CO1
HCID86675911

未命名化合物

结构：COc1cc(CNC(=O)c2cc(C=NO)nc(C)n2)ccc1F
HCID136413230

未命名化合物

PRODUCTS

生成物

1
结构：COc1cc(CNC(=O)c2cc(C3=NO[C@H]([C@H]4CO[C@H](COS(=O)(=O)c5ccc(C)cc5)CO4)C3)nc(C)n2)ccc1F
HCID86675910

未命名化合物

收率 24.3%

PROCEDURE

实验过程

To a stirred solution of N-(4-fluoro-3-methoxybenzyl)-6-((hydroxyimino)methyl)-2-methyl pyrimidine-4-carboxamide (3.84 g, 12.08 mmol, Preparation #9) and ((2S,5S)-5-vinyl-1,4-dioxan-2-yl)methyl 4-methylbenzenesulfonate (3.0 g, 10.06 mmol, Preparation#11) in CHC3 (30 mL), was added iodobenzene diacetate (6.48 g, 20.13 mmol, Aldrich) portion wise (divided in to 4 equal portions and added over a period of 4 hrs). After the addition is completed, the reaction mixture was stirred for another 5 h and quenched with water (100 mL). The product was extracted with DCM (2×100 mL). Combined organic layers were washed with brine solution (100 mL), dried over sodiumsulphate and evaporated to dryness. The residue obtained containing two diastereomers and other impurities was purified by flash column chromatography using silica gel (230-400 mesh) eluting with 40% EtOAc in n-hexane. First eluting compound fractions were combined and evaporated to dryness under reduced pressure, triturated with 40% EtOAc in hexane to afford ((2S,5R)-5-((S)-3-(6-(4-fluoro-3-methoxybenzylcarbamoyl)-2-methylpyrimidin-4-yl)-4,5-dihydroisoxazol-5-yl)-1,4-dioxan-2-yl)methyl 4-methylbenzenesulfonate 1.5 g (24%). 1H NMR (400 MHz, CDCl3): δ 8.48 (s, 1H), 8.28 (t, J=6.4 Hz, 1H), 7.79 (d, J=8 Hz, 2H), 7.36 (d, J=8 Hz, 2H), 7.08-6.96 (m, 2H), 6.90-6.86 (m, 1H), 4.68-4.60 (m, 3H), 4.02-3.93 (m, 2H), 3.88 (s, 3H), 3.85-3.72 (m, 5H), 3.59-3.38 (m, 5H), 2.75 (s, 3H), 2.42 (s, 3H); MS m/z: 615 (m+H)+.

WORKUP

后处理

  1. additionadded over a period of 4 hrs)
  2. additionAfter the addition
  3. customquenched with water (100 mL)
  4. extractionThe product was extracted with DCM (2×100 mL)
  5. washCombined organic layers were washed with brine solution (100 mL)
  6. dry with materialdried over sodiumsulphate
  7. customevaporated to dryness
  8. customThe residue obtained
  9. additioncontaining two diastereomers and other impurities
  10. customwas purified by flash column chromatography
  11. washeluting with 40% EtOAc in n-hexane
  12. customevaporated to dryness under reduced pressure
  13. customtriturated with 40% EtOAc in hexane