Potassium Carbonate → HCID 66702017, compound

HRID 729647Notes

Reaction equation

HRID 729647 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([S:13][C:14]1[N:19]=[C:18]([NH:20][C@H:21]([CH3:31])[CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH:17]=[C:16]([NH2:32])[N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.CO>[CH2:6]([S:13][C:14]1[N:15]=[C:16]([NH:32][S:2]([CH3:1])(=[O:4])=[O:3])[CH:17]=[C:18]([NH:20][C@H:21]([CH3:31])[CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:26])[N:19]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 66701965HCID 66701965, compound

Product 1

HCID 66702017HCID 66702017, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (85 μl) was added to a solution of the subtitle product of step ii) (0.20 g) and N,N-diiosopropylethylamine (0.26 ml) in DCM (10 ml) at 0° C. The ice-bath was removed and stirring maintained for 2 h. The reaction solution was extracted with H2O (2×20 ml) and the organics dried (MgSO4) and concentrated to yield a brown oil. The residue was diluted in methanol (110 ml) and treated with potassium carbonate (0.15 g) for 2 h at room temperature. The volatiles were removed in vacuo and the residue partitioned between EtOAc (20 ml) and H2O (20 ml). The aqueous was further extracted with EtOAc (2×20 ml), the organics combined, dried (MgSO4) and concentrated to yield the subtitle compound as a crude white solid. This material was used directly in the next step. Yield: 0.23 g.

Workup

  1. customThe ice-bath was removed
  2. temperaturemaintained for 2 h
  3. extractionThe reaction solution was extracted with H2O (2×20 ml)
  4. dry with materialthe organics dried (MgSO4)
  5. concentrationconcentrated
  6. customto yield a brown oil
  7. customThe volatiles were removed in vacuo
  8. customthe residue partitioned between EtOAc (20 ml) and H2O (20 ml)
  9. extractionThe aqueous was further extracted with EtOAc (2×20 ml)
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-04f9531477084028a429dbed9be8e8e4
Source dataset
uspto-grants-2009_09
Patent number
US07582644B2

Reaction notes

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