Sodium Cyanide → (3R,4S)-4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-1-(4-iodophenyl)azetidin-2-one

HRID 1437822Notes

Reaction equation

C([O:4][C@H:5]([C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)[CH2:6][CH2:7][C@H:8]1[C:11](=[O:12])[N:10]([C:13]2[CH:18]=[CH:17][C:16]([I:19])=[CH:15][CH:14]=2)[C@@H:9]1[C:20]1[CH:25]=[CH:24][C:23]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])=[CH:22][CH:21]=1)(=O)C.[C-]#N.[Na+]>CO>[Si:27]([O:26][C:23]1[CH:22]=[CH:21][C:20]([C@H:9]2[N:10]([C:13]3[CH:18]=[CH:17][C:16]([I:19])=[CH:15][CH:14]=3)[C:11](=[O:12])[C@@H:8]2[CH2:7][CH2:6][C@@H:5]([C:34]2[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=2)[OH:4])=[CH:25][CH:24]=1)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 15 mg (0.022 mmol) (1S)-3-[(2S,3R)-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1-(4-iodophenyl)-4-oxoazetidin-3-yl]-1-(4-fluorophenyl)propyl acetate (Alternate Example 6, step A) in 1 mL anhydrous methanol under nitrogen atmosphere was added 2 mg of sodium cyanide. The reaction mixture was heated at 50° C. for 1.25 hr at which time the volatiles were removed by a nitrogen stream. The residue was purified by prep. Tlc eluting with EtOAc/hexanes (1/3) to afford the title compound. m/z (ES) 632.3 (MH+), 614.3 (MH−H2O+).

Workup

customwere removed by a nitrogen stream
customThe residue was purified by prep

Sources & evidence

ORD record: ord-cae4dee2d06b43708f444f5f8b160279
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622449B2

Reaction notes

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