Water → HCID 68008756, 화합물

HRID 1429095노트

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HRID 1429095 반응식
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([NH:9][C@@H:10]2[C:24](=[O:25])[N:23]3[CH2:26][C@H:27]([O:29][C:30]4[N:31]=[C:32]5[C:37](=[C:38]6[C:43]=4[CH:42]=[CH:41][CH:40]=[CH:39]6)[CH:36]=[CH:35][CH:34]=[CH:33]5)[CH2:28][C@H:22]3[C:21](=[O:44])[NH:20][C@:19]3([C:46]([O:48]CC)=[O:47])[CH2:45][C@H:18]3[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:8])[CH:3]=1.O.O.[OH-].[Li+]>O1CCCC1.C(O)C>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([NH:9][C@@H:10]2[C:24](=[O:25])[N:23]3[CH2:26][C@H:27]([O:29][C:30]4[N:31]=[C:32]5[C:37](=[C:38]6[C:43]=4[CH:42]=[CH:41][CH:40]=[CH:39]6)[CH:36]=[CH:35][CH:34]=[CH:33]5)[CH2:28][C@H:22]3[C:21](=[O:44])[NH:20][C@:19]3([C:46]([OH:48])=[O:47])[CH2:45][C@H:18]3[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:8])[CH:3]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 68008759HCID 68008759, 화합물

생성물 1

HCID 68008756HCID 68008756, 화합물수율 94%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

To a solution of (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 (Example 18c, 3.4 g, 5.0 mmol) in tetrahydrofuran (16.7 ml), ethanol (8.4 mL), and water (8.4 mL) was added lithium hydroxide monohydrate (1.36 g, 32.5 mmol). The mixture was stirred at 50° C. for 2 h, the solvent was evaporated under reduced pressure, and the residue partitioned between water and ethyl acetate. The aqueous layer was separated, diluted with ethyl acetate, and washed with 1N HCl. The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure to give (2R,6S,13aS,14aR,16aS,Z)-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-carboxylic acid (3.05 g, 94% yield)as a white solid.

후처리

  1. customthe solvent was evaporated under reduced pressure
  2. customthe residue partitioned between water and ethyl acetate
  3. customThe aqueous layer was separated
  4. additiondiluted with ethyl acetate
  5. washwashed with 1N HCl
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-5e3af6f4cb4e43499025a079a38e3bc5
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937041B2

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