Methyl Acetate → HCID 68173591, Verbindung

HRID 538907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 538907
[CH3:1][O:2][C:3](=[O:5])[CH3:4].C([O-])(O)=O.[Na+].[CH3:11][N:12]1[C:16]([SH:17])=[N:15][N:14]=[N:13]1.C[O:19][C:20](C)([CH3:22])[CH3:21].CN1[CH2:29][CH2:28][CH2:27][C:26]1=[O:30]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3](=[O:5])[CH2:4][C@H:26]1[CH2:27][C@@H:28]([CH2:29][S:17][C:16]2[N:12]([CH3:11])[N:13]=[N:14][N:15]=2)[O:19][C:20]([CH3:22])([CH3:21])[O:30]1

Komponenten

7

Edukt 5

HCID 6584Methyl Acetate2×HCID 13387N-methyl-2-pyrrolidoneHCID 15413tert-Butyl methyl etherHCID 516892Sodium Bicarbonate2×HCID 178482017HCID 178482017, Verbindung

Produkt 1

HCID 68173591HCID 68173591, VerbindungAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 74236Tetrabutylammonium BromideKatalysator

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

(4R,6S)-6-(Chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetic acid methyl ester (Compound B, 47.2 g, 0.20 mol) was dissolved in 150 mL of N-methylpyrrolidone. Then NaHCO3 (23.5 g, 0.28 mol) and tetra-n-butyl ammonium bromide (0.5 g) were added. To the stirred mixture was added 1-methyl-1H-tetrazole-5-thiol (MTT, 27.8 g, 0.24 mol). The mixture was heated to 90° C. and kept at this temperature for 18 h. After cooling to 20-25° C., methyl-tert-butyl ether was added (500 mL) and saturated aqueous NaHCO3 (250 mL). Some precipitation was removed by filtration and washed with 100 mL of methyl-tert-butyl ether. The filtrate was washed with 200 mL of saturated aqueous NaHCO3. After drying over Na2SO4, the organic phase was concentrated to give 2-((4R,6S)-2,2-dimethyl-6-((1-methyl-1H-tetrazol-5-ylthio)methyl)-1,3-dioxan-4-yl)acetic acid methyl ester as a solid (Compound C, 45.2 g, yield 71%). 1H NMR (300 MHz, CDCl3) δ 4.40-4.22 (m, 2H), 3.92 (s, 3H), 3.68 (s, 3H), 3.40 (dd, 2H), 2.48 (dd, 2H), 1.74 (dt, 1H), 1.42 (s, 3H), 1.39-1.29 (m, 1H), 1.35 (s, 3H).

Aufarbeitung

  1. temperatureAfter cooling to 20-25° C.
  2. customSome precipitation
  3. customwas removed by filtration
  4. washwashed with 100 mL of methyl-tert-butyl ether
  5. washThe filtrate was washed with 200 mL of saturated aqueous NaHCO3
  6. dry with materialAfter drying over Na2SO4
  7. concentrationthe organic phase was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-d49a255ccc6b403bbb92903099a03d83
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865900B2

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