Calcium Carbonate → HCID 86672777, compound

HRID 1755012Notes

Reaction equation

HRID 1755012 reaction equation
I(Cl)(=O)=O.[I:5](Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1.Cl.Cl.[NH2:22][C:23]1[CH:28]=[C:27]([CH3:29])[C:26]([CH2:30][CH2:31][S:32]([N:35]2[CH2:52][CH2:51][C:38]3([N:42]=[C:41]([CH:43]4[CH2:48][CH2:47][CH:46]([CH3:49])[CH2:45][CH2:44]4)[NH:40][C:39]3=[O:50])[CH2:37][CH2:36]2)(=[O:34])=[O:33])=[C:25]([CH3:53])[CH:24]=1.C(=O)([O-])[O-].[Ca+2].C(=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C.ClCCl>[NH2:22][C:23]1[CH:24]=[C:25]([CH3:53])[C:26]([CH2:30][CH2:31][S:32]([N:35]2[CH2:36][CH2:37][C:38]3([N:42]=[C:41]([CH:43]4[CH2:48][CH2:47][CH:46]([CH3:49])[CH2:45][CH2:44]4)[NH:40][C:39]3=[O:50])[CH2:51][CH2:52]2)(=[O:34])=[O:33])=[C:27]([CH3:29])[C:28]=1[I:5]

Participants

8

Reactant 4

HCID 10112Calcium CarbonateHCID 516892Sodium BicarbonateHCID 56924451Trimethylbenzylammonium DichloroiodateHCID 66817830HCID 66817830, compound

Product 1

HCID 86672777HCID 86672777, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyltrimethylammonium dichloroiodate (324 mg, 0.930 mmol) was added to a mixture of 8-[2-(4-amino-2,6-dimethyl-phenyl)-ethanesulfonyl]-2-(4-methyl-cyclohexyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one dihydrochloride (530 mg, 1.03 mmol) and calcium carbonate (517 mg, 5.17 mmol) in methanol (6 mL)-dichloromethane (15 mL) at room temperature. The mixture was stirred at room temperature for 22 hours, and an aqueous sodium bicarbonate solution and ethyl acetate were then added. The organic layer and the aqueous layer were separated, and the aqueous layer was repeatedly extracted with ethyl acetate three times. The organic layers were combined and washed with saturated brine, and the insoluble matter was then filtered off through celite. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give 8-[2-(4-amino-3-iodo-2,6-dimethyl-phenyl)-ethanesulfonyl]-2-(4-methyl-cyclohexyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one as a pale yellow solid (337 mg, 62%).

Workup

  1. customThe organic layer and the aqueous layer were separated
  2. extractionthe aqueous layer was repeatedly extracted with ethyl acetate three times
  3. washwashed with saturated brine
  4. filtrationthe insoluble matter was then filtered off through celite
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8f047caa183e4cafb94a8fa598a6a30e
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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