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 1437810노트

반응식

HRID 1437810 반응식
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

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

실험 절차

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.

출처 및 근거

ORD 기록
ord-d2393a28a8d24788a4d4ee023cd628d3
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07622449B2

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