Triethylamine → HCID 86756487, compound

HRID 1531321Notes

Reaction equation

HRID 1531321 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]([NH2:32])([CH2:23][C:24]#[C:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:19]([O:21]C)=[O:20])(=[O:17])=[O:16])=[C:11]([C:33]#[CH:34])[CH:10]=2)=[CH:5][CH:4]=1.IS(N)(=O)=O.COC1C=CC(C#C)=CC=1.CCN(CC)CC>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[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]([NH2:32])([CH2:23][C:24]#[C:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:19]([OH:21])=[O:20])(=[O:17])=[O:16])=[C:11]([C:33]#[CH:34])[CH:10]=2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 2510201-Ethynyl-4-methoxybenzeneHCID 18761200Sulfamyl iodideHCID 86756488HCID 86756488, compound

Product 1

HCID 86756487HCID 86756487, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

Methyl 2-[4-(4-Methoxyphenyl)-acetylenylbenzenesulfonyl]-amino-5-phenylpent-4-ynoate: The starting iodo sulfonamide 3a (0.54 g, 1.15 mmol) and 4-methoxyphenylacetylene (0.2 g, 1.49 mmol) are taken in 10 mL of DMF in the presence of 0.32 mL of Et3N, Pd(PPh3)2Cl2 (40.4 mg, 0.058 mmol), and CuI (24 mg, 0.128 mmol). The mixture is then heated to 55° C. for 18 hr. and then partitioned between EtOAc and H2O. The organic layer is washed with 1N HCl, aqueous NaHCO3 and brine, dried over MgSO4, filtered and evaporated to give a residue which is adsorbed onto silica and eluted through a column of flash silica with hexane:EtOAc (4:1 to 2:1 ) to give the desired product.

Workup

  1. customand then partitioned between EtOAc and H2O
  2. washThe organic layer is washed with 1N HCl, aqueous NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give a residue which
  7. washeluted through a column of flash silica with hexane:EtOAc (4:1 to 2:1 )

Sources & evidence

ORD record
ord-a0ae5461681d451e943528a3e4532856
Source dataset
uspto-grants-2001_03
Patent number
US06197770B1

Reaction notes

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