Isobutyric Acid → Allyl 1-{[(alpha-Isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetate

HRID 30517

Reaktionsgleichung

Reaktionsgleichung von HRID 30517
Cl[CH:2]([O:4][C:5]([NH:7][CH2:8][C:9]1([CH2:15][C:16]([O:18][CH2:19][CH:20]=[CH2:21])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:6])[CH3:3].[C:22]([OH:27])(=[O:26])[CH:23]([CH3:25])[CH3:24].CN1CCOCC1.CCCCCC>C(OCC)C>[C:22]([O:27][CH:2]([O:4][C:5]([NH:7][CH2:8][C:9]1([CH2:15][C:16]([O:18][CH2:19][CH:20]=[CH2:21])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:6])[CH3:3])(=[O:26])[CH:23]([CH3:25])[CH3:24]

Komponenten

6

Edukt 4

HCID 6590Isobutyric Acid2×HCID 79724-MethylmorpholineHCID 8058HexaneHCID 9995975Allyl 1-{[(alpha-Chloroethoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetate

Produkt 1

HCID 9999163Allyl 1-{[(alpha-Isobutanoyloxyethoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of compound (14) (38 g, 0.12 mol) in isobutyric acid (55 mL, 52.5 g, 0.6 mol) was added to a mixture of isobutyric acid (55 mL, 52.5 g, 0.6 mol) in N-methylmorpholine (65 mL, 60 g, 0.59 mol) at 0° C. over a period of 30 min. The resulting turbid solution was stirred for 16 h at room temperature. The reaction mixture was diluted with diethyl ether (500 mL) and washed with water (3×200 mL) followed by 10% potassium bicarbonate (4×200 mL) and brine (200 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated to yield a viscous liquid. This crude product was purified by column chromatography on silica gel, eluting with 7.5% ethyl acetate:hexane to give the desired compound (15) as a clear, viscous liquid (37 g, 84% yield). 1H NMR (CDCl3, 400 MHz): δ 1.15 (d, 6H), 1.35-1.58 (m, 10H), 2.31 (s, 2H), 2.51 (m, 1H), 3.19 (d, 2H), 4.56 (d, 2H), 5.24 (dd, 1H), 5.32 (dd, 1H), 5.35 (br. s, 1H), 5.84-5.94 (m, 1H), 6.78 (q, 1H). MS (ESI) m/z 392.24 (M+H+).

Aufarbeitung

  1. washwashed with water (3×200 mL)
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customto yield a viscous liquid
  5. customThis crude product was purified by column chromatography on silica gel
  6. washeluting with 7.5% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4fe61ca5b772457c8464fb77c4ff4df2
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423169B2

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