Tert-butyl 2-(6-(4-(diethoxyphosphoryl)phenyl)pyridin-3-yl)propan-2-ylcarbamate → Diethyl 4-(5-(2-aminopropan-2-yl)pyridin-2-yl)phenylphosphonate

HRID 1525322Notes

Reaction equation

[CH2:1]([O:3][P:4]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]=[CH:19][C:18]([C:21]([NH:24]C(=O)OC(C)(C)C)([CH3:23])[CH3:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]>Cl.O1CCOCC1>[NH2:24][C:21]([C:18]1[CH:17]=[CH:16][C:15]([C:12]2[CH:13]=[CH:14][C:9]([P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:3][CH2:1][CH3:2])=[CH:10][CH:11]=2)=[N:20][CH:19]=1)([CH3:22])[CH3:23]

Participants

Conditions

Temperature: 50 °C

Procedure

tert-butyl 2-(6-(4-(diethoxyphosphoryl)phenyl)pyridin-3-yl)propan-2-ylcarbamate (5.3 g, 11.8 mmol) was dissolved in HCl in dioxane (30 ml), the mixture was stirred at 50° C. for 4 hours. Then evaporated the solvent and the residue diluted with H2O (5 ml), extracted with ethyl acetate and the water phase was adjusted to pH=9 with 1N aqueous NaOH, extracted with ethyl acetate and the organic phase washed with brine and dried, concentrated under vacuo to give the product 33-g.

Workup

customThen evaporated the solvent
additionthe residue diluted with H2O (5 ml)
extractionextracted with ethyl acetate
extractionextracted with ethyl acetate
washthe organic phase washed with brine
customdried
concentrationconcentrated under vacuo

Sources & evidence

ORD record: ord-687fd6b2c5b540e88747899bb1ee27e0
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079930B2

Reaction notes

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