4-Nitrobenzyl 2-diazo-4-((2R,3S)-3-((R)-1-hydroxyethyl)-4-oxoazetidin-2-YL)-3-oxobutanoate → (4-Nitrophenyl)methyl (5R,6S)-6-((1R)-1-hydroxyethyl)-3,7-dioxo-1-azabicyclo(3.2.0)heptane-2-carboxylate

HRID 64811

反応式

[OH:1][C@@H:2]([C@@H:4]1[C@@H:7]([CH2:8][C:9](=[O:26])[C:10]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[O:14])=[N+]=[N-])[NH:6][C:5]1=[O:27])[CH3:3]>C1C=CC=CC=1.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[OH:1][C@@H:2]([C@H:4]1[C:5](=[O:27])[N:6]2[C@@H:7]1[CH2:8][C:9](=[O:26])[CH:10]2[C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1)=[O:14])[CH3:3]

参加物

反応条件

温度: 78 °C

実験手順

A suspension of (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one (56.4 mg, 0.15 mmol) and rhodium (II) acetate (0.1 mg) in dry benzene (3 ml) is deoxygenated by bubbling through nitrogen for 10 minutes. The mixture is then heated to 78° C. for 1 hour. During heating the solid starting material gradually goes into solution. The mixture is then cooled, filtered to remove the catalyst, and the filtrate is concentrated in vacuo to yield (5R,6S) p-nitrobenzyl 6-[(R)-1-hydroxyethyl]-1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate, 51 mg. (98%) as a colorless oil which slowly crystallized at room temperature (22° C.).

後処理

customis deoxygenated
customby bubbling through nitrogen for 10 minutes
temperatureDuring heating the solid
temperatureThe mixture is then cooled
filtrationfiltered
customto remove the catalyst
concentrationthe filtrate is concentrated in vacuo

出典と根拠

ORDレコード: ord-ca3e005acf88490a8935cb5657f4148f
出典データセット: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US04610820

反応式

参加物

反応物 1

生成物 1

試薬・触媒・溶媒 2

反応条件

実験手順

後処理

出典と根拠

関連ノート