Water → HCID 68008756, compound

HRID 1429095Notes

Reaction equation

HRID 1429095 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 68008756HCID 68008756, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5e3af6f4cb4e43499025a079a38e3bc5
Source dataset
uspto-grants-2015_01
Patent number
US08937041B2

Reaction notes

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