Diethylamine → HCID 59596703, compound

HRID 2264822Notes

Reaction equation

HRID 2264822 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]#[CH:16])[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])[CH3:3].I[C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=1.C(NCC)C.C(OCC)(=O)C>C(OCC)C.[Cu]I.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>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([C:16]#[C:15][CH2:14][C@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:10]([O:12][CH3:13])=[O:11])=[CH:19][CH:20]=1

Participants

8

Reactant 4

HCID 8021DiethylamineHCID 8857Ethyl AcetateHCID 115221-Bromo-4-iodobenzeneHCID 11817013(S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-ynoate

Product 1

HCID 59596703HCID 59596703, compoundYield 69.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

A solution of methyl (2S)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-pentynoate (D64, 1.020 g, 4.49 mmol), prepared by an analogous procedure to the one described hereinabove, 4-Iodo-bromobenzene (1.524 g, 5.38 mmol), diethylamine (2.28 ml, 1.62 g, 22.12 mmol), CuI (84 mg, 0.441 mmol) and Pd(PPh3)2Cl2 (156 mg, 0.22 mmol) in diethyl ether (10 ml) was stirred at room temperature for 24 h. Ethyl acetate was added and the organic layer was washed with aqueous ammonium chloride solution, dried (Na2SO4), filtered and evaporated under vacuum. The residue was purified via flash chromatography using a gradient of cyclohexanes and ethyl acetate (98:2 to 80:20) to afford the title compound (1.199 g, 69%). MS: (ES/+) m/z: 404, 406 [MH+], C17H20BrNO4 requires 404. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 7.56 (d, 1H), 7.45 (d, 1H), 7.32 (d, 1H), 4.30 (m, 1H), 3.67 (s, 3H), 2.82 (m, 2H), 1.40 and 1.38 (2xs, 9H).

Workup

  1. washthe organic layer was washed with aqueous ammonium chloride solution
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated under vacuum
  5. customThe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-2f4e2deb04994c1e92b764f67b4699be
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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