Methyl iodide → HCID 70223159, compound

HRID 1531327Notes

Reaction equation

HRID 1531327 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([C:18]([NH:29][CH3:30])([CH2:23][C:24]#[C:25][CH2:26][O:27][CH3:28])[C:19]([O:21]C)=[O:20])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.O=S(Cl)Cl.CI.C([O-])([O-])=O.[Cs+].[Cs+]>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([S:15]([C:18]([NH:29][CH3:30])([CH2:23][C:24]#[C:25][CH2:26][O:27][CH3:28])[C:19]([OH:21])=[O:20])(=[O:16])=[O:17])=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 24386Thionyl ChlorideHCID 70224459HCID 70224459, compound

Product 1

HCID 70223159HCID 70223159, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-{[4′-Methoxy-(1,1′-biphenyl)-4-yl]-sulfonyl}-N-methyl-amino-6-methoxyhex-4-ynoate: The acid 51 (500 mg, 1.23 mmole) is dissolved in 20 mL of MeOH and treated with 8 mL of SOCl2. The resulting mixture is stirred at RT for 18 hr. and then evaporated. The residual solid is dissolved in 10 mL of dimethylacetamide and treated with methyl iodide (0.092 mL, 1.47 mmole) in the presence of 600 mg of Cs2CO3. The resulting mixture is stirred for 2 hr and then partitioned between EtOAc and H2O. The organic layer is washed with water and then brine, dried over MgSO4, filtered and evaporated to give a yellow oil. The title acid is prepared from compound 52b as described for compound 46f.

Workup

  1. customand then evaporated
  2. dissolutionThe residual solid is dissolved in 10 mL of dimethylacetamide
  3. stirringThe resulting mixture is stirred for 2 hr
  4. custompartitioned between EtOAc and H2O
  5. washThe organic layer is washed with water
  6. dry with materialbrine, dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give a yellow oil

Sources & evidence

ORD record
ord-ce26ec1a96144f549da386b36c877eab
Source dataset
uspto-grants-2001_03
Patent number
US06197770B1

Reaction notes

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