Hydrochloric Acid → HCID 19359181, compound

HRID 376793Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]([I:12])=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].Cl.C(N(CC)CC)C.[CH3:21][C:22]([O:25][C:26](ON=C(C1C=CC=CC=1)C#N)=[O:27])([CH3:24])[CH3:23]>O.O1CCCC1>[C:22]([O:25][C:26]([C:4]1[C:3]([CH2:2][NH2:1])=[CH:11][CH:10]=[C:9]([I:12])[C:5]=1[C:6]([OH:8])=[O:7])=[O:27])([CH3:24])([CH3:23])[CH3:21]

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 3-aminomethyl-6-iodobenzoic acid.circle-solid.HCl (8.0 g, 26 mmol) and triethylamine (8.7 g, 86 mmol) in 32 ml of H2O, was added to a solution of Boc-ON (8.0 g, 32 mmol) in 23 ml of tetrahydrofuran cooled to 0° C. The reaction mixture was stirred at room temperature for overnight, and the volatile compounds were removed by concentration under reduced pressure. The residue was diluted with H2O, washed with ether, acidified to pH 3 with 1N HCl, and extracted with ethyl acetate. The extracts were washed with H2O, brine, dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure. This material was triturated from ether to provide the title compound (5.7 g, 59%) as a white powder; mp 182° C. (dec);

Workup

customthe volatile compounds were removed by concentration under reduced pressure
additionThe residue was diluted with H2O
washwashed with ether
extractionextracted with ethyl acetate
washThe extracts were washed with H2O, brine
dry with materialdried over anhydrous magnesium sulfate
customevaporated to dryness under reduced pressure
customThis material was triturated from ether

Sources & evidence

ORD record: ord-32d7cd1282744dc98f3f995f46cdc7b0
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06022523

Reaction notes

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