1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-{[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-azido-methyl}-benzonitrile

HRID 1161087Notes

Reaction equation

[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16](O)[C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])=[CH:12][CH:11]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2].N12CCCN=C1CCCCC2.C1(P([N:57]=[N+:58]=[N-:59])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1>[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([N:57]=[N+:58]=[N-:59])[C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])=[CH:12][CH:11]=2)=[C:6]([CH2:28][CH2:29][CH3:30])[C:5]=1[OH:31])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3-{[4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-hydroxy-methyl}-benzonitrile (3 g, 7.22 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (2.3 mL, 15.2 mmol), diphenylphosphoryl azide (3.3 mL, 15.2 mmol) and tetrahydrofuran (20 mL) is stirred at 50° C. 2 hr. The mixture is concentrated and the crude residue is purified via silica chromatography eluting with hexanes to 7:3 hexanes:ethyl acetate to give the title compound 1.77 g, 56% as a white solid. LCMS M−1 439.

Workup

custom2 hr
concentrationThe mixture is concentrated
customthe crude residue is purified via silica chromatography
washeluting with hexanes to 7:3 hexanes

Sources & evidence

ORD record: ord-eeefd2a4dc294284aebcde28fa4d286e
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816523B2

Reaction notes

Loading…