Nitrogen → HCID 68295599, compound

HRID 572477Notes

Reaction equation

HRID 572477 reaction equation
I[C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:12]([OH:17])[C@@H:13]([OH:16])[C:14]#[CH:15].CCN(CC)CC.N#N>C(#N)C.CCOC(C)=O.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:16][C@H:13]([CH2:12][OH:17])[C:14]#[C:15][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

9

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 69132Benzoic acid, 2-iodo-, methyl esterHCID 14142903HCID 14142903, compound

Product 1

HCID 68295599HCID 68295599, compoundYield 86%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of methyl 2-iodobenzoate (2.312 ml, 15.26 mmol), (2S)-3-butyne-1,2-diol (1.380 g, 16.03 mmol), and Et3N (10.64 ml, 76 mmol) in Acetonitrile (25.2 ml) was degassed with N2 for 10 min and treated with CuI (0.581 g, 3.05 mmol) and Pd(PPh3)4 (0.264 g, 0.229 mmol) and the reaction mixture was heated to 80° C. After 20 min, the reaction mixture was cooled to ambient temperature. The reaction mixture was diluted with EtOAc and washed with saturated aqueous NH4Cl, water and brine. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate-hexanes 0-100%) to afford the title compound (2.88 g, 13.08 mmol, 86% yield) as a beige solid: Rt=0.54 min, ES+ MS: 221 (M+1).

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. washwashed with saturated aqueous NH4Cl, water and brine
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (ethyl acetate-hexanes 0-100%)

Sources & evidence

ORD record
ord-9b9f31b10df94b2f81e33a95abe2c843
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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