Hydrochloric Acid → HCID 68008759, 화합물

HRID 1429094노트

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HRID 1429094 반응식
[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

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 769473-Methyl-5-isoxazolecarboxylic acidHCID 81531DiisopropylethylamineHCID 68008345HCID 68008345, 화합물

생성물 1

HCID 68008759HCID 68008759, 화합물수율 80%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0ad81805356149f6a5a1c18871d7f4e2
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937041B2

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