Cesium carbonate → 3-(Tert-butoxycarbonylamino-methyl)-5-methyl-hexanoic acid 1-isobutyryloxy-ethyl ester

HRID 1361046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1361046
C(=O)([O-])[O-].[Cs+].[Cs+].C(O[C:10]([O:12][CH:13]([O:15][C:16](=[O:32])[CH2:17][CH:18]([CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:19][CH:20]([CH3:22])[CH3:21])[CH3:14])=[O:11])C.IC(O[C:37](=O)[CH:38](C)[CH3:39])C>CO.CC#N>[C:10]([O:12][CH:13]([O:15][C:16](=[O:32])[CH2:17][CH:18]([CH2:23][NH:24][C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[CH2:19][CH:20]([CH3:21])[CH3:22])[CH3:14])(=[O:11])[CH:38]([CH3:39])[CH3:37]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 14633820Propanoic acid, 2-methyl-, 1-iodoethyl esterHCID 723692293-(Tert-butoxycarbonylamino-methyl)-5-methyl-hexanoic acid 1-ethyloxycarbonyloxy-ethyl ester

Produkt 1

HCID 723692273-(Tert-butoxycarbonylamino-methyl)-5-methyl-hexanoic acid 1-isobutyryloxy-ethyl esterAusbeute 27,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

Cesium carbonate (0.365 g, 1.12 mmol) was dissolved in methanol (5 mL) and S-form of compound 4 (0.500 g, 1.28 mmol) was added. The solution was stirred for 4 hours at room temperature and concentrated to dryness. The residue was diluted with CH3CN (7.5 mL), and compound 14 (0.945 g, 3.56 mmol) and CH3CN (5 mL) were then added. After stirring overnight at room temperature, the reaction solution was filtered and concentrated to give 1 g of the crude product, which was then purified by chromatography on a column of silica gel (70-230 mesh, elution: EA/Hexane=1:4). Compound 3-(tert-butoxycarbonylamino-methyl)-5-methyl-hexanoic acid 1-isobutyryloxy-ethyl ester 15 (0.13 g) was obtained with 27% yield. 1HNMR (CDCl3, 500 MHz) δ0.87-0.92 (m, 6H), 1.10-1.21 (m, 2H), 1.55 (d, J=5 Hz, 6H), 1.44 (s, 9H), 1.48 (d, J=5.5 Hz, 3H), 1.52-1.59 (m, 2H), 2.06-2.12 (m, 1H), 2.28-2.35 (m, 2H), 2.49-2.57 (m, 1H), 2.93-3.06 (m, 1H), 3.12-3.22 (m, 1H), 4.62-4.73 (m, 1H), 6.84 (q, J=5.5 Hz, 1H).

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. additionwere then added
  3. stirringAfter stirring overnight at room temperature
  4. filtrationthe reaction solution was filtered
  5. concentrationconcentrated
  6. customto give 1 g of the crude product, which
  7. customwas then purified by chromatography on a column of silica gel (70-230 mesh, elution: EA/Hexane=1:4)

Quellen und Nachweise

ORD-Eintrag
ord-e32920b6c0f040e7900d315776f2d569
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879906B2

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