Hydrochloric Acid → Hydrochloric Acid

HRID 1429102Notes

Reaction equation

HRID 1429102 reaction equation
[CH:1]1([S:4]([NH:7][C:8]([C@@:10]23[CH2:25][C@H:24]2[CH2:23][C:22]([F:27])([F:26])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]([NH:28]C(=O)OC(C)(C)C)[C:15](=[O:36])[N:14]2[CH2:37][C@H:38]([O:40][C:41]4[N:42]=[C:43]5[C:48](=[C:49]6[C:54]=4[CH:53]=[CH:52][CH:51]=[CH:50]6)[CH:47]=[CH:46][CH:45]=[CH:44]5)[CH2:39][C@H:13]2[C:12](=[O:55])[NH:11]3)=[O:9])(=[O:6])=[O:5])[CH2:3][CH2:2]1.[ClH:56]>C(OCC)(=O)C.O1CCOCC1>[NH2:28][C@@H:16]1[C:15](=[O:36])[N:14]2[CH2:37][C@H:38]([O:40][C:41]3[N:42]=[C:43]4[C:48](=[C:49]5[C:54]=3[CH:53]=[CH:52][CH:51]=[CH:50]5)[CH:47]=[CH:46][CH:45]=[CH:44]4)[CH2:39][C@H:13]2[C:12](=[O:55])[NH:11][C@:10]2([C:8]([NH:7][S:4]([CH:1]3[CH2:3][CH2:2]3)(=[O:6])=[O:5])=[O:9])[CH2:25][C@H:24]2[CH2:23][C:22]([F:26])([F:27])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[ClH:56]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 68172046HCID 68172046, compound

Product 2

HCID 313Hydrochloric AcidYield 99.2%HCID 68009051HCID 68009051, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl (2R,6S,13aS,14aR,16aS)-14a-(cyclopropylsulfonylcarbamoyl)-12,12-difluoro-5,16-dioxo-2-(phenanthridin-6-yloxy)octadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-ylcarbamate (Example 19, 195 mg, 0.249 mmol) in ethyl acetate (1 mL) stiffing at room temperature was added 4 N hydrogen chloride (1.24 mL, 5.0 mmol) in dioxane. The reaction mixture was stirred for 4 h, and then the solvent was evaporated under reduced pressure. The residue was triturated with ethyl acetate and the product was filtered as a white solid. The solid was dissolved in methanol and the solvent was evaporated to provide the title compound (2R,6S,13aS,14aR,16aS)-6-amino-N-(cyclopropylsulfonyl)-12,12-difluoro-5,16-dioxo-2-(phenanthridin-6-yloxy)octadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxamide, Hydrochloric Acid (178 mg, 0.247 mmol, 99% yield).

Workup

  1. customstiffing at room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was triturated with ethyl acetate
  4. filtrationthe product was filtered as a white solid
  5. dissolutionThe solid was dissolved in methanol
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6a278e424d0f49aa8c8eb11d56c4f5ad
Source dataset
uspto-grants-2015_01
Patent number
US08937041B2

Reaction notes

Loading…