Hydrogen Bromide → HCID 66961648, compound

HRID 1363468Notes

Reaction equation

[BrH:1].[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C:4](=[O:12])O1.[CH2:13]([OH:15])[CH3:14]>>[C:13]([O:12][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[CH2:2][Br:1])(=[O:15])[CH3:14]

Participants

Reactant 3

HCID 260Hydrogen Bromide

HCID 702Ethanol

HCID 780921,4-dihydro-3H-2-benzopyran-3-one

Product 1

HCID 66961648HCID 66961648, compound

Conditions

Temperature: 70 °C

Procedure

An ethanol solution of hydrogen bromide (25%, 10 ml) was added to 1,4-dihydro-3H-isochromene-3-one (500 mg) and stirred at 70° C. overnight. After removing the solvent, the residue was roughly purified with a silica gel chromatography (hexane-ethyl acetate) to obtain a crude material of [2-(bromomethyl)phenyl]ethyl acetate. Methyl 3-(4-aminophenyl)-2-[(2,6-dichlorobenzoyl)amino]propionate (520 mg), triethylamine (490 μl) and DMF (5 ml) were added to the crude material and stirred at 125° C. for six hours. After removing the solvent, the residue was purified with a silica gel chromatography (hexane-ethyl acetate) to obtain methyl 2-[(2,6-dichlorobenzoyl)amino]-3-(4-{[2-(2-ethoxy-2-oxoethyl)benzyl]amino}phenyl)propionate (510 mg).

Workup

customAfter removing the solvent
customthe residue was roughly purified with a silica gel chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record: ord-b6c655aaf6b749639796c2956505de61
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884204B2

Reaction notes

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