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Dimethylformamide → (+/-)-cis-1-(Acetyloxy)-6-methoxy-3,3,14-trimethyl-7-oxo-2,3,7,14-tetrahydro-1h-benzo[b]chromeno[6,5-g][1,8]naphthyridin-2-yl [(tert-butoxycarbonyl)amino]acetate

HRID 18038
ノート
印刷プレビュー

反応式

HRID 18038 の反応式
C1(N=C=N[CH:10]2[CH2:15]CCCC2)CCCCC1.[OH:16][C@@H:17]1[C:34]2[C:33]3[N:32]([CH3:35])[C:31]4[N:30]=[C:29]5[CH:36]=[CH:37][CH:38]=[CH:39][C:28]5=[CH:27][C:26]=4[C:25](=[O:40])[C:24]=3[C:23]([O:41][CH3:42])=[CH:22][C:21]=2[O:20][C:19]([CH3:44])([CH3:43])[C@@H:18]1[OH:45].[C:46]([O:50][C:51]([NH:53][CH2:54][C:55]([OH:57])=O)=[O:52])([CH3:49])([CH3:48])[CH3:47].CN(C)C=[O:61]>>[C:46]([O:50][C:51]([NH:53][CH2:54][C:55]([O:45][C@@H:18]1[C@H:17]([O:16][C:15](=[O:61])[CH3:10])[C:34]2[C:33]3[N:32]([CH3:35])[C:31]4[N:30]=[C:29]5[CH:36]=[CH:37][CH:38]=[CH:39][C:28]5=[CH:27][C:26]=4[C:25](=[O:40])[C:24]=3[C:23]([O:41][CH3:42])=[CH:22][C:21]=2[O:20][C:19]1([CH3:43])[CH3:44])=[O:57])=[O:52])([CH3:47])([CH3:48])[CH3:49]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 11327222(+/-)-cis-1,2-Dihydroxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7h-benzo[b]chromeno[6,5-g][1,8]naphthyridin-7-one

生成物 1

HCID 91322932(+/-)-cis-1-(Acetyloxy)-6-methoxy-3,3,14-trimethyl-7-oxo-2,3,7,14-tetrahydro-1h-benzo[b]chromeno[6,5-g][1,8]naphthyridin-2-yl [(tert-butoxycarbonyl)amino]acetate

反応条件

温度
0 °C

実験手順

Slowly add 0.6 mmol of dicyclohexylcarbodiimide to a solution, at 0° C., of 0.5 mmol of the compound of Example 3 and 0.5 mmol of 2-[(tert-butoxycarbonyl)amino]acetic acid in 10 ml of dimethylformamide. The reaction mixture is maintained at 0° C. for 5 hours and then at ambient temperature for 16 hours. After filtration and evaporation under reduced pressure, the residue is dissolved in 2 ml of anhydrous pyridine, 2 ml of acetic anhydride are added, and stirring is carried out for 48 hours at ambient temperature in darkness. After concentration of the reaction mixture under reduced pressure, chromatography of the residue on silica gel (dichloromethane) allows the expected product to be isolated.

後処理

  1. customat 0° C.
  2. filtrationAfter filtration and evaporation under reduced pressure
  3. dissolutionthe residue is dissolved in 2 ml of anhydrous pyridine
  4. addition2 ml of acetic anhydride are added
  5. waitis carried out for 48 hours at ambient temperature in darkness
  6. customto be isolated

出典と根拠

ORDレコード
ord-d281b54b4b4e46799a6826aa78101bc8
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07741325B2

反応ノート

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