Hydrochloric Acid → HCID 68008759、化合物

HRID 1429094ノート

反応式

HRID 1429094 の反応式
[NH2:1][C@@H:2]1[C:16](=[O:17])[N:15]2[CH2:18][C@H:19]([O:21][C:22]3[N:23]=[C:24]4[C:29](=[C:30]5[C:35]=3[CH:34]=[CH:33][CH:32]=[CH:31]5)[CH:28]=[CH:27][CH:26]=[CH:25]4)[CH2:20][C@H:14]2[C:13](=[O:36])[NH:12][C@:11]2([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:37][C@H:10]2[CH:9]=[CH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.Cl.[CH3:44][C:45]1[O:49][N:48]=[C:47]([C:50](O)=[O:51])[CH:46]=1.C(N(C(C)C)C(C)C)C>ClCCl>[CH3:44][C:45]1[O:49][N:48]=[C:47]([C:50]([NH:1][C@@H:2]2[C:16](=[O:17])[N:15]3[CH2:18][C@H:19]([O:21][C:22]4[N:23]=[C:24]5[C:29](=[C:30]6[C:35]=4[CH:34]=[CH:33][CH:32]=[CH:31]6)[CH:28]=[CH:27][CH:26]=[CH:25]5)[CH2:20][C@H:14]3[C:13](=[O:36])[NH:12][C@:11]3([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:37][C@H:10]3[CH:9]=[CH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)=[O:51])[CH:46]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 769473-Methyl-5-isoxazolecarboxylic acidHCID 81531DiisopropylethylamineHCID 68008345HCID 68008345、化合物

生成物 1

HCID 68008759HCID 68008759、化合物収率 80%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a suspension of (2R,6S,13aS,14aR,16aS,Z)-ethyl 6-amino-5,16-dioxo-2-(phenanthridin-6-yloxy)-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo [1,2-a][1,4]diazacyclopentadecine-14a-carboxylate, Hydrochloric Acid (Example 18b, 5.00 g, 8.24 mmol), 5-methylisoxazole-3-carboxylic acid (1.15 g, 9.06 mmol) and 2-(3H41,2,31triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (3.44 g, 9.06 mmol) in dichloromethane (82 ml) was added N-ethyl-N-isopropylpropan-2-amine (5.03 ml, 28.8 mmol). The mixture was stirred at rt for 2 h, and then quenched with saturated aqueous sodium carbonate solution. The organic layer was washed with 1N HCl, separated, filtered, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to provide a white foam. This material was purified flash chromatography on silica gel (4:1 dichloromethane/ethyl acetate) to give (2R,6S,13aS,14aR,16aS,Z)-ethyl 6-(5-methylisoxazole-3-carboxamido)-5,16-dioxo-2-(phenanthridin-6-yloxy)-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (4.5 g, 80% yield).

後処理

  1. customquenched with saturated aqueous sodium carbonate solution
  2. washThe organic layer was washed with 1N HCl
  3. customseparated
  4. filtrationfiltered
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto provide a white foam
  8. customThis material was purified flash chromatography on silica gel (4:1 dichloromethane/ethyl acetate)

出典と根拠

ORDレコード
ord-0ad81805356149f6a5a1c18871d7f4e2
出典データセット
uspto-grants-2015_01
特許番号
US08937041B2

反応ノート

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