Hydrochloric Acid → HCID 68879129, compound

HRID 724548Notes

Reaction equation

HRID 724548 reaction equation
C[O:2][C:3](=[O:63])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([CH2:23][C@@H:24]2[OH:27])[C@:20]2([CH3:21])[C@@H:15]([CH2:16][C@@H:17]([O:28][CH2:29][CH2:30][N:31]([C:33]4[CH:38]=[CH:37][C:36]([C@H:39]5[CH2:56][C@@:54]6([CH3:55])[C@@H:50]([CH2:51][CH2:52][C@:53]6([OH:60])[C:57]#[C:58][CH3:59])[C@H:49]6[C:40]5=[C:41]5[C:46]([CH2:47][CH2:48]6)=[CH:45][C:44](=[O:61])[CH2:43][CH2:42]5)=[CH:35][CH:34]=4)[CH3:32])[CH2:18][CH2:19]2)[CH2:14][C@H:13]3[OH:62])[CH2:10][CH2:9]1)[CH3:7].[OH-].[K+].Cl>CCO>[OH:62][C@@H:13]1[CH2:14][C@H:15]2[C@:20]([CH3:21])([CH2:19][CH2:18][C@H:17]([O:28][CH2:29][CH2:30][N:31]([C:33]3[CH:38]=[CH:37][C:36]([C@H:39]4[CH2:56][C@@:54]5([CH3:55])[C@@H:50]([CH2:51][CH2:52][C@:53]5([OH:60])[C:57]#[C:58][CH3:59])[C@H:49]5[C:40]4=[C:41]4[C:46]([CH2:47][CH2:48]5)=[CH:45][C:44](=[O:61])[CH2:43][CH2:42]4)=[CH:35][CH:34]=3)[CH3:32])[CH2:16]2)[C@@H:22]2[C@@H:12]1[C@H:11]1[C@:25]([CH3:26])([C@@H:24]([OH:27])[CH2:23]2)[C@@H:8]([C@H:6]([CH3:7])[CH2:5][CH2:4][C:3]([OH:63])=[O:2])[CH2:9][CH2:10]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-1ceed512070c4695a0c6408bd56ba52d
Source dataset
uspto-grants-2006_11
Patent number
US07141559B2

Reaction notes

Loading…