Tributylphosphine → 5(S)-(Isoxazol-3-yl-aminomethyl)-3-(4-morpholinophenyl)-oxazolidin-2-one

HRID 1582370

Reaktionsgleichung

Reaktionsgleichung von HRID 1582370
OC[C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH2:4]1.C(OC(N[C:29]1[CH:33]=[CH:32][O:31][N:30]=1)=O)(C)(C)C.C(P(CCCC)CCCC)CCC.[N:47]([C:57](N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[O:31]1[CH:32]=[CH:33][C:29]([CH:57]([NH2:47])[C@H:3]2[O:7][C:6](=[O:8])[N:5]([C:9]3[CH:14]=[CH:13][C:12]([N:15]4[CH2:16][CH2:17][O:18][CH2:19][CH2:20]4)=[CH:11][CH:10]=3)[CH2:4]2)=[N:30]1

Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 20725693(R)-5-(hydroxymethyl)-3-(4-morpholinophenyl)oxazolidin-2-oneHCID 21992950tert-Butyl 1,2-oxazol-3-ylcarbamate

Produkt 1

HCID 698904955(S)-(Isoxazol-3-yl-aminomethyl)-3-(4-morpholinophenyl)-oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5(R)-Hydroxymethyl-3-(4-morpholinophenyl)oxazolidin-2-one (prepared by analogy to the 3-fluoro compound—see WO95/07271; 0.50 g, 1.80 mmol), 3-t-butyloxycarbonylamino-isoxazole (0.50 g, 2.70 mmol), tri-n-butylphosphine (0.66 ml, 2.70 mmol), and 1,1′-(azodicarbonyl)-di-piperidine (0.68 g, 2.70 mmol) were reacted in anhydrous THF (30 ml) using the general method of Reference Example 15. The reaction was then purified by MPLC (Merck 9385 silica, 70% ethyl acetate in iso-hexane) and the solvent removed under reduced pressure to give a solid which was triturated with ether to give the title compound as an off-white solid. 1H-NMR (300 MHz, DMSO-d6): δ=1.50 (s, 9H), 3.08 (t, 4H), 3.70-3.80 (m, 5H), 3.93-4.01 (m, 1H), 4.14-4.30 (m, 2H), 4.95 (m, 1H), 6.88 (s, 1H), 6.99 (d, 2H), 7.40 (d, 2H), 8.81 (s, 1H). MS: ESP+ (M+H)+=445.

Aufarbeitung

  1. customThe reaction was then purified by MPLC (Merck 9385 silica, 70% ethyl acetate in iso-hexane)
  2. customthe solvent removed under reduced pressure
  3. customto give a solid which
  4. customwas triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-4c95cb43c66d4c578150478395b167e3
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06734200B1

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