1,2-Dichloroethane → HCID 59332878, compound

HRID 1879990Notes

Reaction equation

HRID 1879990 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[CH2:32]([O:34][C:35](=[O:45])[C@H:36]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[NH2:37])[CH3:33]>CN(C=O)C.O>[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:37][C@@H:36]([CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:35]([O:34][CH2:32][CH3:33])=[O:45])=[O:6]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 729302-Aminonicotinic acidHCID 757711-HydroxybenzotriazoleHCID 76506Phenylalanine ethyl ester

Product 1

HCID 59332878HCID 59332878, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of aminonicotinic acid (2.74 g, 20 mmol) in anhydrous DMF (100 mL) was added EDC (4.2 g, 22 mmol), HOBt (2.97 g, 22 mmol) and triethylamine (8.2 mL, 60 mmol). L-phenylalanine ethyl ester (4.97 g, 22 mmol) was added and the reaction was stirred overnight. Water (100 mL) was added and the mixture was extracted with methylene chloride (4×100 mL), dried over MgSO4 and concentrate. The compound was purified by silica gel chromatography (gradient CH2Cl2 to 10% MeOH/CH2Cl2) to afford the title compound as a yellow oil (6.2 g, 98%): 1H NMR (300 MHz, CDCl3) δ 8.78 (d, J=7.6 Hz, 1H), 8.09 (d, J=5.0 Hz, 1H), 7.89 (d, J=7.9 Hz, 1H), 7.31-7.18 (m, 5H), 6.96 (s, 2H), 6.60 (dd, J=7.7 Hz, 4.7 Hz, 1H), 4.63-4.56 (m, 1H), 4.10 (q, J=7.0 Hz, 2H), 3.15-3.09 (m, 2H), 1.05 (t, J=7.0 Hz, 3H); ESI MS m/z 314 [C17H19N3O3+H]+

Workup

  1. extractionthe mixture was extracted with methylene chloride (4×100 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrate
  4. customThe compound was purified by silica gel chromatography (gradient CH2Cl2 to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3b5a60e38da44654927ec800f50ee136
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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