tert-Butanol → HCID 68461294, compound

HRID 505431Notes

Reaction equation

[CH3:1][C:2]1[C:3](C(O)=O)=[N:4][C:5]([C:10]([OH:12])=[O:11])=[CH:6][C:7]=1[O:8][CH3:9].C([N:18]([CH2:21]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.[C:40]([OH:44])([CH3:43])([CH3:42])[CH3:41]>O1CCOCC1.C(OCC)(=O)C>[CH3:1][C:2]1[C:3]([NH:18][C:21]([O:44][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:30])=[N:4][C:5]([C:10]([OH:12])=[O:11])=[CH:6][C:7]=1[O:8][CH3:9]

Participants

Conditions

Temperature: 80 °C

Procedure

2.0 g of methyl 4-methoxy-pyridin-2,6-dicarboxylic acid (compound E3) are suspended in 40 ml of dioxane and 5.63 ml of tert-butanol. 2.63 ml of triethylamine and 4.08 ml of diphenylphosphoryl azide are added to the mixture. Subsequently, the reaction mixture is heated at 80° C. for 72 h with vigorous stirring under a nitrogen atmosphere. Further 0.41 ml each of diphenylphosphoryl azide are added after 24 h and 48 h, respectively. Thereafter, the mixture is cooled to room temperature, diluted with 300 ml of ethyl acetate and extracted four times each with 80 ml of sat sodium hydrogencarbonate. The organic layer is dried using sodium sulphate, filtered with suction and concentrated in vacuum. The crude product (5.08 g) is purified by chromatography (eluent: toluene/ethyl acetate 5:1) to afford 1.10 g of the title compound as a colorless oil. TSP-MS: 283.1 [MH+]. TLC: Rf=0.24 (toluene/ethyl acetate 5:1).

Workup

temperatureThereafter, the mixture is cooled to room temperature
extractionextracted four times each with 80 ml of sat sodium hydrogencarbonate
customThe organic layer is dried
filtrationfiltered with suction
concentrationconcentrated in vacuum
customThe crude product (5.08 g) is purified by chromatography (eluent: toluene/ethyl acetate 5:1)

Sources & evidence

ORD record: ord-6504f45985934d73bd57fe3bf06d8a18
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781453B2

Reaction notes

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