Sodium Cyanide → N-[3-(4-{(2S,3R)-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-1-yl}phenyl)prop-2-yn-1-yl]methanesulfonamide

HRID 1437813Notes

Reaction equation

C([O:4][C@H:5]([C:41]1[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=1)[CH2:6][CH2:7][C@H:8]1[C:11](=[O:12])[N:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][CH2:21][NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:15][CH:14]=2)[C@@H:9]1[C:27]1[CH:32]=[CH:31][C:30]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])=[CH:29][CH:28]=1)(=O)C.[C-]#N.[Na+]>CO>[Si:34]([O:33][C:30]1[CH:29]=[CH:28][C:27]([C@@H:9]2[C@@H:8]([CH2:7][CH2:6][C@@H:5]([C:41]3[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=3)[OH:4])[C:11](=[O:12])[N:10]2[C:13]2[CH:14]=[CH:15][C:16]([C:19]#[C:20][CH2:21][NH:22][S:23]([CH3:26])(=[O:24])=[O:25])=[CH:17][CH:18]=2)=[CH:32][CH:31]=1)([C:37]([CH3:40])([CH3:38])[CH3:39])([CH3:35])[CH3:36]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 40 mg (0.059 mmol) (1S)-3-[(2S,3R)-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1-(4-{3-[(methylsulfonyl)amino]prop-1-yn-1-yl}phenyl)-4-oxoazetidin-3-yl]-1-(4-fluorophenyl)propyl acetate (intermediate of step B) in 1 mL anhydrous methanol under nitrogen atmosphere was added 1 mg of sodium cyanide. The reaction mixture was heated at 50° C. for 4 hrs at which time the volatiles were removed by a nitrogen stream. The residue was purified by prep. Tlc eluting with EtOAc/hexanes (3/1) to afford the title compound. m/z (ES) 637.2 (MH+), 619.1 M−H2O+).

Workup

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

Sources & evidence

ORD record: ord-81008343d728408ba491a79eba7429b1
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622449B2

Reaction notes

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