Borane → HCID 86701260, Verbindung

HRID 2276061Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2276061
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:17][O:16][C:15](=[O:18])[C@H:14]([CH2:19][C:20](O)=[O:21])[C@@H:13]([O:23][C:24](=[O:28])[CH:25]([CH3:27])[CH3:26])[C@H:12]([CH3:29])[O:11][C:10]1=[O:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].B>C1COCC1>[C:24]([O:23][C@@H:13]1[C@@H:14]([CH2:19][CH2:20][OH:21])[C:15](=[O:18])[O:16][CH2:17][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[C:10](=[O:30])[O:11][C@H:12]1[CH3:29])(=[O:28])[CH:25]([CH3:27])[CH3:26]

Komponenten

4

Edukt 2

HCID 6331BoraneHCID 86701256HCID 86701256, Verbindung

Produkt 1

HCID 86701260HCID 86701260, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

To a solution of 2-((3S,7R,8R,9S)-3-(tert-butoxycarbonylamino)-8-(isobutyryloxy)-9-methyl-2,6-dioxo-1,5-dioxonan-7-yl)acetic acid (2.0 g, 4.64 mmol) in THF (15 mL) was added borane (1.0 M in THF, 5.56 mL, 5.56 mmol) at 0° C. After 15 min the ice bath was removed and the reaction was allowed to warm to room temperature (about 22° C.). After an additional 1.5 h, the reaction was quenched with EtOAc (10 mL) and washed successively with 0.5 N HCl (10 mL) and sat'd aqueous NaHCO3 (10 mL). The phases were separated and the organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give the title compound (1.38 g, 72%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 5.40-5.19 (m, 2H), 5.07 (t, J=9.9 Hz, 1H), 4.95-4.75 (m, 2H), 3.74-3.52 (m, 3H), 2.83-2.68 (m, 1H), 2.61 (dt, J=13.9, 7.0 Hz, 1H), 2.07-1.90 (m, 1H), 1.70-1.52 (m, 1H), 1.44 (s, 9H), 1.27 (d, J=6.3 Hz, 3H), 1.20 (d, J=7.0 Hz, 6H); ESIMS m/z 440.3 ([M+Na]+).

Aufarbeitung

  1. customAfter 15 min the ice bath was removed
  2. customthe reaction was quenched with EtOAc (10 mL)
  3. washwashed successively with 0.5 N HCl (10 mL)
  4. customThe phases were separated
  5. dry with materialthe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7cd347e9c76c4d57aea26531d1b3137d
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09131690B2

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