Hydrochloric Acid → HCID 19359164, compound

HRID 376792Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH2:11][NH2:12].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]([CH2:11][NH2:12])=[C:2]([Cl:1])[CH:10]=[CH:9][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 4-chloro-3-aminomethylbenzoic acid.circle-solid.HCl (6.7 g, 30 mmol) and triethylamine (9.3 g, 92 mmol) in 50 ml of H2O, was added to a solution of Boc-ON (9.2 g, 38 mmol) in 50 ml of tetrahydrofuran cooled to 0° C. The reaction mixture was stirred at room temperature 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 with ether-hexane to provide the title compound (7.4 g, 87%) as a white powder. mp 159° 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 with ether-hexane

Sources & evidence

ORD record: ord-02820cd03e0d4c90a0986262f401e3fe
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06022523

Reaction notes

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