Hydrochloric Acid → HCID 68879129, compound

HRID 2112313Notes

Reaction equation

HRID 2112313 reaction equation
[OH:1][C@@H:2]1[CH2:26][C@H:25]2[C@:20]([CH3:61])([CH2:21][CH2:22][C@H:23]([O:27][CH2:28][CH2:29][N:30]([C:32]3[CH:37]=[CH:36][C:35]([C@H:38]4[CH2:55][C@@:53]5([CH3:54])[C@@H:49]([CH2:50][CH2:51][C@:52]5([OH:59])[C:56]#[C:57][CH3:58])[C@H:48]5[C:39]4=[C:40]4[C:45]([CH2:46][CH2:47]5)=[CH:44][C:43](=[O:60])[CH2:42][CH2:41]4)=[CH:34][CH:33]=3)[CH3:31])[CH2:24]2)[C@@H:19]2[C@@H:3]1[C@H:4]1[C@:16]([CH3:63])([C@@H:17]([OH:62])[CH2:18]2)[C@@H:7]([C@H:8]([CH3:15])[CH2:9][CH2:10][C:11]([O:13]C)=[O:12])[CH2:6][CH2:5]1.[OH-].[K+].Cl>CCO>[OH:1][C@@H:2]1[CH2:26][C@H:25]2[C@:20]([CH3:61])([CH2:21][CH2:22][C@H:23]([O:27][CH2:28][CH2:29][N:30]([C:32]3[CH:37]=[CH:36][C:35]([C@H:38]4[CH2:55][C@@:53]5([CH3:54])[C@@H:49]([CH2:50][CH2:51][C@:52]5([OH:59])[C:56]#[C:57][CH3:58])[C@H:48]5[C:39]4=[C:40]4[C:45]([CH2:46][CH2:47]5)=[CH:44][C:43](=[O:60])[CH2:42][CH2:41]4)=[CH:34][CH:33]=3)[CH3:31])[CH2:24]2)[C@@H:19]2[C@@H:3]1[C@H:4]1[C@:16]([CH3:63])([C@@H:17]([OH:62])[CH2:18]2)[C@@H:7]([C@H:8]([CH3:15])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium Hydroxide2×HCID 131726114HCID 131726114, compound

Product 1

HCID 68879129HCID 68879129, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of the compound of Example 1I (17.28 g, 20.0 mmol, 91% chemical potency, therefore 15.72 g, 18.2 mmol) in EtOH (173 mL) at 5° C. was charged 3N KOH (33.3 mL, 100 mmol) at a rate to maintain an internal temperature <7° C. The reaction was stirred at 5° C. for 17 hour. The reaction mixture was neutralized with 3N HCl (33.3 mL, 100 mmol) while maintaining the internal temperature <10 ° C. (end pH was adjusted from 4.63 to 4.87 with 0.2 mL of 3N KOH). The reaction mixture crystallized after a few minutes post addition of 3N HCl. The reaction mixture was allowed to warm to ambient temperature, seeded (20 mg of seed crystals), warmed to 40° C. for 3 hours and slowly cooled back to ambient temperature stirred an additional 16 hours. The slurry was filtered, washed and dried to provide 14.30 g (92.4%) of the title compound.

Workup

  1. temperatureto maintain an internal temperature <7° C
  2. customThe reaction mixture crystallized after a few minutes post addition of 3N HCl
  3. temperatureto warm to ambient temperature
  4. temperaturewarmed to 40° C. for 3 hours
  5. temperatureslowly cooled back to ambient temperature
  6. stirringstirred an additional 16 hours
  7. filtrationThe slurry was filtered
  8. washwashed
  9. customdried

Sources & evidence

ORD record
ord-834aae004ea54b61a90f8c792b9d3394
Source dataset
uspto-grants-2009_04
Patent number
US07521439B2

Reaction notes

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