反応 #77801

ord-7554628260ef42abad6b46ff21b8ca04

反応方程式

Methyl iodide

DBU

$CCCCC[C@H](O)/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)NS(C)(=O)=O)[C@@H](O)C[C@H]1O$

N-{(Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((S)-(E)-3-hydroxyoct-1-enyl)cyclopentyl]hept-5-enoyl}methanesulfonamide

→

$CCCCC[C@H](O)/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)N(C)S(C)(=O)=O)[C@@H](O)C[C@H]1O$

title compound

$CCCCC[C@H](O)/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)N(C)S(C)(=O)=O)[C@@H](O)C[C@H]1O$

N-{(Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((S)-(E)-3-hydroxyoct-1-enyl)cyclopentyl]-hept-5-enoyl}-N-methylmethanesulfonamide

反応物

Methyl iodide

DBU

$CCCCC[C@H](O)/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)NS(C)(=O)=O)[C@@H](O)C[C@H]1O$

N-{(Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((S)-(E)-3-hydroxyoct-1-enyl)cyclopentyl]hept-5-enoyl}methanesulfonamide

試薬

なし

溶媒

acetone

EtOAc

反応条件

詳細条件

See reaction.notes.procedure_details.

後処理

1
洗浄washed with water (2×) and brine
2
濃縮then concentrated in vacuo

実験手順

Methyl iodide (38 μL, 0.61 mmol) and DBU (45 μL, 0.30 mmol) were added to a solution of N-{(Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((S)-(E)-3-hydroxyoct-1-enyl)cyclopentyl]hept-5-enoyl}methanesulfonamide (44 mg, 0.10 mmol) in acetone (1.5 mL). After stirring for 2.5 h at room temperature, the reaction was diluted with EtOAc, washed with water (2×) and brine then concentrated in vacuo to afford the title compound. See FIG. 1.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US06706755B2uspto-grants-2004_03