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Iodo benzene diacetate → ((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

HRID 572654
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 572654
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:15]=[C:14]([CH:16]=[N:17][OH:18])[N:13]=[C:12]([CH3:19])[N:11]=2)=[O:9])=[CH:4][C:3]=1[O:22][CH3:23].[CH3:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([O:34][CH2:35][C@@H:36]2[CH2:41][O:40][C@@H:39]([CH:42]=[CH2:43])[CH2:38][O:37]2)(=[O:33])=[O:32])=[CH:27][CH:26]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>>[CH3:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([O:34][CH2:35][C@@H:36]2[CH2:41][O:40][C@@H:39]([C@H:42]3[O:18][N:17]=[C:16]([C:14]4[CH:15]=[C:10]([C:8](=[O:9])[NH:7][CH2:6][C:5]5[CH:20]=[CH:21][C:2]([F:1])=[C:3]([O:22][CH3:23])[CH:4]=5)[N:11]=[C:12]([CH3:19])[N:13]=4)[CH2:43]3)[CH2:38][O:37]2)(=[O:32])=[O:33])=[CH:27][CH:26]=1
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Komponenten

4

Edukt 3

HCID 12217721Iodo benzene diacetateHCID 86675911((2S,5S)-5-vinyl-1,4-dioxan-2-yl)methyl 4-methylbenzenesulfonateHCID 136413230N-(4-fluoro-3-methoxybenzyl)-6-((hydroxyimino)methyl)-2-methylpyrimidine-4-carboxamide

Produkt 1

HCID 86675910((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-methylbenzenesulfonateAusbeute 24,3 %

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-aa6766e118e64cff939f8b65299eaddf
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09029409B2

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