Hydrochloric Acid → HCID 54202017, compound

HRID 1835634Notes

Reaction equation

HRID 1835634 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:66]2[N:65]=[CH:64][N:63]=[C:53]([NH:54][C:55](=[O:62])[C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)[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:41])=[O:40])([CH2:18][O:19][Si:20]([C:33]([CH3:35])([CH3:34])[CH3:36])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[O:7][C@@H:6]([N:49]2[C:66]3[N:65]=[CH:64][N:63]=[C:53]([NH:54][C:55](=[O:62])[C:56]4[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=4)[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 54453330HCID 54453330, compound

Product 1

HCID 54202017HCID 54202017, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methyl alcohol solution (3.0 ml) of Compound 40 (167.9 mg, 0.182 mmol), potassium carbonate (15.0 mg, 0.109 mmol) was added at room temperature, and the mixture was stirred for 15 minute 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 41 (140.5 mg, 0.160 mmol, 88%).

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-2d458fa43e1f415394cdcac255c5726b
Source dataset
uspto-grants-2004_08
Patent number
US06770748B2

Reaction notes

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