Triethylamine → (1S)-3-[(2S,3R)-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1-(4-iodophenyl)-4-oxoazetidin-3-yl]-1-(4-fluorophenyl)propyl acetate

HRID 1437811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1437811
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([OH:30])[CH2:9][CH2:10][C@@H:11]2[C@@H:14]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)[N:13]([C:22]3[CH:27]=[CH:26][C:25]([I:28])=[CH:24][CH:23]=3)[C:12]2=[O:29])=[CH:4][CH:3]=1.FC(F)(F)S(O[Si](C(C)(C)C)(C)C)(=O)=[O:34].[Si:46](N1C=CN=C1)([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47].C(N([CH2:63][CH3:64])CC)C>C(Cl)Cl>[C:63]([O:30][C@H:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:9][CH2:10][C@H:11]1[C:12](=[O:29])[N:13]([C:22]2[CH:23]=[CH:24][C:25]([I:28])=[CH:26][CH:27]=2)[C@@H:14]1[C:15]1[CH:20]=[CH:19][C:18]([O:21][Si:46]([C:49]([CH3:50])([CH3:51])[CH3:52])([CH3:47])[CH3:48])=[CH:17][CH:16]=1)(=[O:34])[CH3:64]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 1713851-((1,1-Dimethylethyl)dimethylsilyl)-1H-imidazoleHCID 10098065(3R,4S)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-1-(4-iodophenyl)azetidin-2-one

Produkt 1

HCID 68975033(1S)-3-[(2S,3R)-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1-(4-iodophenyl)-4-oxoazetidin-3-yl]-1-(4-fluorophenyl)propyl acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 0.5 g. (0.894 mmol, 1 equiv.) (3R,4S)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-1-(4-iodophenyl)azetidin-2-one (i-6) in 5 mL anhydrous methylene chloride under inert atmosphere at 0° C. was added 0.36 mL (1.564 mmol, 1.75 equiv.) tert-butyldimethylsilyl trifluoromethanesulfonate, 0.175 mL (0.894 mmol, 1 equiv.) N-tert-butyldimethylsilylimidazole and 0.311 mL (2.234 mmol, 2.5 equivalents) triethylamine. The resulting reaction mixture was stirred at 0° C. for 15 minutes then quenched by the addition of 5 mL of sat. aq. solution of sodium carbonate. The resulting mixture was transferred to a separatory funnel, extracted with methylene chloride (3×5 mL). The combined organic extracts were dried over anhydrous Na2SO4 filtered and the solvent removed under vacuum. The residue was purified by prep. Tlc eluting with EtOAc/hexanes (2/1) to afford the title compound. m/z (ES) 696.0 (M+Na+), 614.0 (M−OAc+).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customthen quenched by the addition of 5 mL of sat. aq. solution of sodium carbonate
  3. customThe resulting mixture was transferred to a separatory funnel
  4. extractionextracted with methylene chloride (3×5 mL)
  5. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customthe solvent removed under vacuum
  8. customThe residue was purified by prep

Quellen und Nachweise

ORD-Eintrag
ord-099b69c9d5844e988b42a4973ad6ad47
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07622449B2

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