Triethylamine → N-(3-{4-[(2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-2-(4-hydroxyphenyl)-4-oxoazetidin-1-yl]phenyl}prop-2-yn-1-yl)methanesulfonamide

HRID 600186

Reaction equation

HRID 600186 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([OH:37])[CH2:16][CH2:17][C@@H:18]2[C@@H:21]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[N:20]([C:29]3[CH:34]=[CH:33][C:32](I)=[CH:31][CH:30]=3)[C:19]2=[O:36])=[CH:11][CH:10]=1.[CH2:38]([NH:41][S:42]([CH3:45])(=[O:44])=[O:43])[C:39]#[CH:40]>CN(C=O)C.[Cu]I>[F:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([OH:37])[CH2:16][CH2:17][C@H:18]2[C:19](=[O:36])[N:20]([C:29]3[CH:34]=[CH:33][C:32]([C:40]#[C:39][CH2:38][NH:41][S:42]([CH3:45])(=[O:44])=[O:43])=[CH:31][CH:30]=3)[C@@H:21]2[C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10098065(3R,4S)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-1-(4-iodophenyl)azetidin-2-oneHCID 14025440N-(Prop-2-yn-1-yl)methanesulfonamide

Product 1

HCID 67055618N-(3-{4-[(2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-2-(4-hydroxyphenyl)-4-oxoazetidin-1-yl]phenyl}prop-2-yn-1-yl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

Triethylamine (7 equivalents) is added to a solution of (3R,4S)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-1-(4-iodophenyl)azetidin-2-one (i-6) (1.00 equivalent), N-prop-2-yn-1-ylmethanesulfonamide (i-5) (1.50 equivalents), tetrakistriphenylphosphine palladium(0) (0.15 equivalents) and copper(I) iodide (0.30 equivalents) in DMF (0.1 M concentration with respect to final product) under a nitrogen atmosphere and the resulting solution aged at room temperature. After completion of reaction, the volatiles are evaporated in vacuo and the crude residue can be purified by flash chromatography on silica gel to afford the title compound.

Sources & evidence

ORD record
ord-40df4eaf520145d9a1cf54849cd8871a
Source dataset
uspto-grants-2011_03
Patent number
US07901893B2

Linked notes

Loading…