Trityl chloride → HCID 86610956, compound

HRID 505428Notes

Reaction equation

HRID 505428 reaction equation
[CH3:1][C:2]1[C:3]([NH2:13])([C:10]([OH:12])=[O:11])[NH:4][CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C(N(C(C)C)CC)(C)C.[C:23](Cl)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][C:2]1[C:3]([NH:13][C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)([C:10]([OH:12])=[O:11])[NH:4][CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 81531DiisopropylethylamineHCID 86610957HCID 86610957, compound2×

Product 1

HCID 86610956HCID 86610956, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Procedure

1.70 g of methyl 2-amino-4-methoxy-picolinic acid (compound C6) are dissolved in 44 ml of dichloromethane. Subsequently, 1.92 ml of diisopropylethylamine, 690 mg of tetrabutylammonium iodide, and 3.12 g of trityl chloride are added. The solution is stirred for 48 h at room temperature. Thereafter, the mixture is extracted three times each with 50 ml of sat sodium hydrogencarbonate solution. The organic layer is dried using sodium sulphate, filtered with suction and concentrated in vacuum. The crude product (5.38 g) is purified by chromatography (eluent: toluene/ethyl acetate 5:1) to afford 3.49 g of the title compound as a colorless oil. TSP-MS: 425.2 [MH+]. TLC: Rf=0.37 (toluene/ethyl acetate 5:1).

Workup

  1. extractionThereafter, the mixture is extracted three times each with 50 ml of sat sodium hydrogencarbonate solution
  2. customThe organic layer is dried
  3. filtrationfiltered with suction
  4. concentrationconcentrated in vacuum
  5. customThe crude product (5.38 g) is purified by chromatography (eluent: toluene/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-3a7605c788024345bc0a4704b8482d8e
Source dataset
uspto-grants-2010_08
Patent number
US07781453B2

Reaction notes

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