Hydrochloric Acid → HCID 136393286, compound

HRID 1387734Notes

Reaction equation

HRID 1387734 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@@:8]([CH2:37][O:38][S:39]([C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=2)(=[O:41])=[O:40])([CH2:18][O:19][Si:20]([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:7][C@H:6]1[N:49]1[C:64]2[N:63]=[C:56]([NH:57][C:58](=[O:62])[CH:59]([CH3:61])[CH3:60])[NH:55][C:53](=[O:54])[C:52]=2[N:51]=[CH:50]1)(=O)C.C(=O)([O-])[O-].[K+].[K+].Cl>CO>[CH2:11]([O:10][C@@H:9]1[C@@:8]([CH2:37][O:38][S:39]([C:42]2[CH:43]=[CH:44][C:45]([CH3:48])=[CH:46][CH:47]=2)(=[O:40])=[O:41])([CH2:18][O:19][Si:20]([C:33]([CH3:34])([CH3:36])[CH3:35])([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[O:7][C@@H:6]([N:49]2[C:64]3[N:63]=[C:56]([NH:57][C:58](=[O:62])[CH:59]([CH3:60])[CH3:61])[NH:55][C:53](=[O:54])[C:52]=3[N:51]=[CH:50]2)[C@@H:5]1[OH:4])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 136094466HCID 136094466, compound

Product 1

HCID 136393286HCID 136393286, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methyl alcohol solution (3.0 ml) of Compound 44 (137.0 mg, 0.151 mmol), potassium carbonate (15.8 mg, 0.113 mmol) was added at room temperature, and the mixture was stirred for 45 minutes at room temperature. Concentrated hydrochloric acid was added to the reaction mixture to neutralize it, whereafter the system was extracted 3 times with methylene chloride. The organic phase was washed with a saturated sodium chloride solution, and then dried over sodium sulfate. The solvents were distilled off under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (CHCl3-MeOH, 30:1) to obtain a white powder, Compound 45 (83.4 mg, 0.097 mmol, 64%).

Workup

  1. extractionwhereafter the system was extracted 3 times with methylene chloride
  2. washThe organic phase was washed with a saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. distillationThe solvents were distilled off under reduced pressure
  5. customthe resulting crude product was purified by silica gel column chromatography (CHCl3-MeOH, 30:1)

Sources & evidence

ORD record
ord-d2ac734115fa4c158b44b97715cbaddc
Source dataset
uspto-grants-2001_07
Patent number
US06268490B1

Reaction notes

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