Hydrochloric Acid → HCID 68008687, compound

HRID 1429073Notes

Reaction equation

HRID 1429073 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:26]([O:28][C:29]3[CH:38]=[N:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=3)[CH2:27][C@H:21]2[C:20](=[O:39])[NH:19][C@:18]2([C:41]([O:43]CC)=[O:42])[CH2:40][C@H:17]2[CH2:16][C:15]([F:47])([F:46])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].Cl>O1CCCC1.C(O)C.O.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:26]([O:28][C:29]3[CH:38]=[N:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=3)[CH2:27][C@H:21]2[C:20](=[O:39])[NH:19][C@:18]2([C:41]([OH:43])=[O:42])[CH2:40][C@H:17]2[CH2:16][C:15]([F:46])([F:47])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68008906HCID 68008906, compound

Product 1

HCID 68008687HCID 68008687, compoundYield 79%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R,6S,13aS,14aR,16aS)-ethyl 6-(tert-butoxycarbonylamino)-12,12-difluoro-5,16-dioxo-2-(quinoxalin-2-yloxy)octadecahydrocyclopropa[e]pyrrolo [1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (Example 1h, 14.6 mg, 0.022 mmol) in tetrahydrofuran (55.3 μl), ethanol (27.6 μl) and Water (27.6 μl) was added lithium hydroxide monohydrate (4.19 mg, 0.100 mmol). The reaction mixture was stirred at room temperature overnight, diluted with ethyl acetate and cooled to 0° C. The reaction mixture was neutralized with HCl (4 N in dioxane, 25 μl; diluted with ethyl acetate), stirred at room temperature and dried over anhydrous sodium sulfate. The mixture was filtered and evaporated under reduced pressure and the residue was purified by prep-TLC (elute with dichloromethane/methanol=5/1) to provide the title compound (2R,6S,13aS,14aR,16aS)-6-(tert-butoxycarbonylamino)-12,12-difluoro-5,16-dioxo-2-(quinoxalin-2-yloxy)octadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylic acid (11.04 mg, 0.017 mmol, 79% yield).

Workup

  1. temperaturecooled to 0° C
  2. stirringstirred at room temperature
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe mixture was filtered
  5. customevaporated under reduced pressure
  6. customthe residue was purified by prep-TLC (elute with dichloromethane/methanol=5/1)

Sources & evidence

ORD record
ord-a082a48f80464693b35869dea082e2a7
Source dataset
uspto-grants-2015_01
Patent number
US08937041B2

Reaction notes

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