Hydrochloric Acid → (R)-2-Methyl-2-(2-trimethylsilanyl-ethoxymethyl)-but-3-enoic acid

HRID 2285347노트

반응식

HRID 2285347 반응식
C([C@@H]1COC(=O)N1[C:10](=[O:23])[C@@:11]([CH3:22])([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[CH2:13])(C)C.OO.O.[OH-].[Li+].S(S([O-])=O)([O-])(=O)=[O:30].[Na+].[Na+].Cl>O1CCCC1.O>[CH3:22][C@:11]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:19])([CH3:20])[CH3:21])([CH:12]=[CH2:13])[C:10]([OH:23])=[O:30]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 168937Lithium hydroxide, monohydrateHCID 656671Sodium PyrosulfiteHCID 86709642(R)-4-Isopropyl-3-[(R)-2-methyl-2-(2-trimethylsilanyl-ethoxymethyl)-but-3-enoyl]-oxazolidin-2-one

생성물 1

HCID 86709643(R)-2-Methyl-2-(2-trimethylsilanyl-ethoxymethyl)-but-3-enoic acid수율 88%

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

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온도
0 °C

실험 절차

A cooled (0° C.) solution of (R)-4-isopropyl-3-[(R)-2-methyl-2-(2-trimethylsilanyl-ethoxymethyl)-but-3-enoyl]-oxazolidin-2-one (543.3 mg, 1.591 mmol) in tetrahydrofuran/water (15 mL, 2:1) was subsequently treated with hydrogen peroxide (30%, 820 μL, 7.955 mmol) and lithium hydroxide monohydrate (133.5 mg, 3.181 mmol). After stirring at 0° C. for 2 h, the reaction was quenched with solid sodium metabisulfite (3 g, 16 mmol). After stirring at room temperature for 30 min, the mixture was acidified with hydrochloric acid (1 M) to pH 2, the aqueous layer was extracted with dichloromethane (2×). The organics were combined, filtered through a phase separator and the volatiles were removed in vacuo. The residue was purified by silica gel chromatography using a 50 g Isolute cartridge eluted with a continuous gradient of iso-hexanes/ethyl acetate 1:0 to 4:1 to afford the title compound (322.3 mg, 88%) as a colourless oil. 1H NMR (300 MHz, CDCl3) δ 0.03 (s, 9H), 0.98 (app t, J=8.5 Hz, 2H), 1.34 (s, 3H), 3.46 (d, J=8.9 Hz, 1H), 3.57-3.67 (m, 3H), 5.19-5.29 (m, 2H), 6.00 (dd, J=17.4, 10.7 Hz, 1H), 10.80 (br s, 1H).

후처리

  1. stirringAfter stirring at room temperature for 30 min
  2. extractionthe aqueous layer was extracted with dichloromethane (2×)
  3. filtrationfiltered through a phase separator
  4. customthe volatiles were removed in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluted with a continuous gradient of iso-hexanes/ethyl acetate 1:0 to 4:1

출처 및 근거

ORD 기록
ord-dd8f1c8e05a44ecc9d741e2009b8cd10
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145441B2

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