Triethylamine → HCID 58100142, compound

HRID 1696849Notes

Reaction equation

HRID 1696849 reaction equation
C(N(CC)CC)C.I[C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17][CH2:18][N:19]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]2=[O:29])=[CH:11][CH:10]=1.[CH2:30]([O:37][C:38](=[O:44])[NH:39][CH2:40][CH2:41][C:42]#[CH:43])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1.[Cu]I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:30]([O:37][C:38](=[O:44])[NH:39][CH2:40][CH2:41][C:42]#[C:43][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17][CH2:18][N:19]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]2=[O:29])=[CH:11][CH:10]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 21185506HCID 21185506, compoundHCID 58100104HCID 58100104, compound

Product 1

HCID 58100142HCID 58100142, compoundYield 72.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution containing triethylamine (100 mL), copper (I) iodide (0.50 g, 2.60 mmol) and 57 (7.00 g, 17.40 mmol) dissolved in anhydrous tetrahydrofuran (100 mL) was stirred at room temperature. The reaction flask was vacuumed and then purged with nitrogen three times. The solution was treated with bis(triphenylphosphine) palladium(II) dichloride (1.20 g, 1.70 mmol) and continued to stir at room temperature for 30 min. The reaction mixture was then treated with but-3-ynylcarbamic acid benzyl ester (4.25 g, 20.90 mmol). The reaction was allowed to stir at room temperature for 16 h. The solution was filtered and the filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography eluting with 0-100% ethyl acetate in hexanes to afford the desired product 58 (6.0 g, 72%) as a brown solid: 1H NMR (500 MHz, CD2Cl2) δ 7.85 (dd, 2H), 7.74 (dd, 2H), 7.35-7.32 (m, 5H), 7.27 (d, 2H), 7.22 (d, 2H), 5.08 (s, 2H), 3.93 (t, 2H), 3.39 (t, 2H), 2.81 (t, 2H), 2.62 (t, 2H); m/z (ESI) 477 [C30H24N2O4+H]+.

Workup

  1. custompurged with nitrogen three times
  2. stirringto stir at room temperature for 30 min
  3. stirringto stir at room temperature for 16 h
  4. filtrationThe solution was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe resulting residue was purified by column chromatography
  7. washeluting with 0-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-271f262cdb644f5cb02551ecd308eeae
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

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