Hydrochloric Acid → HCID 68008425, compound

HRID 1429097Notes

Reaction equation

HRID 1429097 reaction equation
[F:1][C:2]1([F:54])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]([NH:17][C:18]([C:20]2[CH:24]=[C:23]([CH3:25])[O:22][N:21]=2)=[O:19])[C:10](=[O:26])[N:9]2[CH2:27][C@H:28]([O:30][C:31]3[N:32]=[C:33]4[C:38](=[C:39]5[C:44]=3[CH:43]=[CH:42][CH:41]=[CH:40]5)[CH:37]=[CH:36][CH:35]=[CH:34]4)[CH2:29][C@H:8]2[C:7](=[O:45])[NH:6][C@:5]2([C:47]([O:49]C(C)(C)C)=[O:48])[CH2:46][C@H:4]2[CH2:3]1.Cl>C(OCC)(=O)C.O1CCOCC1>[F:54][C:2]1([F:1])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]([NH:17][C:18]([C:20]2[CH:24]=[C:23]([CH3:25])[O:22][N:21]=2)=[O:19])[C:10](=[O:26])[N:9]2[CH2:27][C@H:28]([O:30][C:31]3[N:32]=[C:33]4[C:38](=[C:39]5[C:44]=3[CH:43]=[CH:42][CH:41]=[CH:40]5)[CH:37]=[CH:36][CH:35]=[CH:34]4)[CH2:29][C@H:8]2[C:7](=[O:45])[NH:6][C@:5]2([C:47]([OH:49])=[O:48])[CH2:46][C@H:4]2[CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68008469HCID 68008469, compound

Product 1

HCID 68008425HCID 68008425, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (2R,6S,13aS,14aR,16aS)-tert-butyl 12,12-difluoro-6-(5-methylisoxazole-3-carboxamido)-5,16-dioxo-2-(phenanthridin-6-yloxy)octadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (Example 18h, 20 mg, 0.027 mmol) in ethyl acetate (100 μl) stiffing at rt was added 4N hydrogen chloride (134 μl, 0.536 mmol) in dioxane. The reaction mixture was stirred for 24 h, and the solvent was evaporated under reduced pressure. The residue was purified by preparative thin layer chromatography (10% methanol/dichloromethane) to provide the title compound (2R,6S,13aS,14aR,16aS)-12,12-difluoro-6-(5-methylisoxazole-3-carboxamido)-5,16-dioxo-2-(phenanthridin-6-yloxy)octadecahydrocyclopropa[e]pyrrolo [1,2-a][1,4]diazacyclopentadecine-14a-carboxylic (10.2 mg, 55%)

Workup

  1. customstiffing at rt
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by preparative thin layer chromatography (10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-788e19e204e44168a550e0ba977c7b5f
Source dataset
uspto-grants-2015_01
Patent number
US08937041B2

Reaction notes

Loading…