Water → HCID 68008756、化合物

HRID 1429095ノート

反応式

HRID 1429095 の反応式
[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

参加物

6

反応物 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 68008759HCID 68008759、化合物

生成物 1

HCID 68008756HCID 68008756、化合物収率 94%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5e3af6f4cb4e43499025a079a38e3bc5
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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