THF TFA water → N-(2-methyl-3-oxo-2,3,4,5-tetrahydro-1H-2-benzazepin-4-yl)-(E)-(2R,3R,4S,5R)-3,4,5-trihydroxy-2-methoxy-8,8-dimethylnon-6-enamide

HRID 1986535

反応式

[CH3:1][C:2]([CH3:34])([CH3:33])/[CH:3]=[CH:4]/[C@H:5]1[O:10]C(C)(C)[O:8][C@@H:7]([C@@H:13]([O:30][CH3:31])[C:14]([NH:16][CH:17]2[CH2:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[CH2:20][N:19]([CH3:28])[C:18]2=[O:29])=[O:15])[C@H:6]1[OH:32].FC(F)(F)C(O)=O.O1CCCC1.O>ClCCl.CO>[CH3:28][N:19]1[C:18](=[O:29])[CH:17]([NH:16][C:14](=[O:15])[C@H:13]([O:30][CH3:31])[C@H:7]([OH:8])[C@@H:6]([OH:32])[C@H:5]([OH:10])/[CH:4]=[CH:3]/[C:2]([CH3:34])([CH3:33])[CH3:1])[CH2:23][C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[CH2:20]1

参加物

反応条件

温度: 0 °C

実験手順

24 mg (50 μmol) of product 5, and then 2 ml of a cold trifluoroacetic acid/tetrahydrofuran/water mixture (1.6/1.6/1.0 v/v/v) are successively introduced, at 0° C., into a round-bottomed flask equipped with a magnetic stirrer. This mixture is maintained at 0° C. until the starting material has disappeared on TLC (1 hour) (90/10 v/v dichloromethane/methanol). The solvent is evaporated off under reduced pressure and 2 ml of methanol are added to the residue, which is reevaporated under reduced pressure. This last step is repeated a second time and the residue is dissolved in 5 ml of water in a minimum volume of methanol (0.5 ml). The solution is freeze-dried, giving the expected product Example 1 quantitatively in the form of a foam.

後処理

customequipped with a magnetic stirrer
customThe solvent is evaporated off under reduced pressure and 2 ml of methanol
additionare added to the residue, which
customis reevaporated under reduced pressure
dissolutionthe residue is dissolved in 5 ml of water in a minimum volume of methanol (0.5 ml)
customThe solution is freeze-dried

出典と根拠

ORDレコード: ord-9312fc2b21c34e3080f1c5962164142f
出典データセット: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07550453B2

反応式

参加物

反応物 2

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

関連ノート