Hydrochloric Acid → HCID 136393286, compound

HRID 1835636Notes

Reaction equation

HRID 1835636 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-6b532588304048949362b03e5cbd7ec0
Source dataset
uspto-grants-2004_08
Patent number
US06770748B2

Reaction notes

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