Triethylamine → HCID 86602245, compound

HRID 2116691Notes

Reaction equation

HRID 2116691 reaction equation
[NH2:1][C@H:2]([CH2:8][C:9]1[CH:14]=[C:13](I)[C:12]([NH2:16])=[C:11]([Cl:17])[CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(N(CC)CC)C.[CH3:25][Si:26]([C:29]#[CH:30])([CH3:28])[CH3:27]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I.O>[NH2:1][C@H:2]([CH2:8][C:9]1[CH:14]=[C:13]([C:30]#[C:29][Si:26]([CH3:28])([CH3:27])[CH3:25])[C:12]([NH2:16])=[C:11]([Cl:17])[CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 69365101HCID 69365101, compound

Product 1

HCID 86602245HCID 86602245, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

Under protective argon gas a mixture of 235 mg (0.64 mmol) ethyl (R)-2-amino-3-(4-amino-3-chloro-5-iodo-phenyl)-propionate, 45.9 mg (0.064 mmol) bis-(triphenylphosphine)-palladium(II)-dichloride, 6.0 mg (0.032 mmol) copper(I)- iodide and 15 ml triethylamine was combined with 0.19 ml (1.32 mmol) trimethylsilylacetylene and stirred for 3 hours at ambient temperature. The reaction mixture was combined with 30 ml of water and extracted with 40 ml of ethyl acetate. The organic phase was dried over sodium sulphate, evaporated down under reduced pressure and the residue was purified by column chromatography through silica gel.

Workup

  1. extractionextracted with 40 ml of ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customevaporated down under reduced pressure
  4. customthe residue was purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-86952bb7b08d41deb08b8782bd61e8ca
Source dataset
uspto-grants-2008_10
Patent number
US07439237B2

Reaction notes

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