Borane;pyridine → p-NO2-Bn-Cyclen

HRID 377012

Reaction equation

N1C=CC=CC=1.B.[N+:8]([C:11]1[CH:33]=[CH:32][C:14]([CH2:15][CH:16]2[C:27](=O)[NH:26][CH2:25][C:24](=O)[NH:23][CH2:22][C:21](=O)[NH:20][CH2:19][C:18](=O)[NH:17]2)=[CH:13][CH:12]=1)([O-:10])=[O:9]>N1C=CC=CC=1>[N+:8]([C:11]1[CH:33]=[CH:32][C:14]([CH2:15][C@H:16]2[CH2:27][NH:26][CH2:25][CH2:24][NH:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18][NH:17]2)=[CH:13][CH:12]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 120 °C

Procedure

Borane-pyridine (available from Aldrich) is added to a suspension of 2-(4-nitrobenzyl)-3,6,9,12-tetraoxo-1,4,7,10-tetraazacyclododecane in pyridine. The mixture is heated under reflux at 120° C. for 14 hours. The solvent is removed under reduced pressure. The residue is taken up in methanol and heated under reflux for 2 hours. The solvent is removed under reduced pressure. The residue is dissolved in methanol and re-evaporated. The solid residue is purified by chromatography on reverse phase Baker G18 silica gel available from J.T. Baker, Inc., Phillipsburg, N.J. Conversion of this product to nitro-benzyl-DOTA is accomplished via the procedure discussed in Renn et al., Bioconj. Chem., 3:563-569, 1992 or as set forth is subpart A above.

Workup

temperatureThe mixture is heated
customThe solvent is removed under reduced pressure
temperatureheated
temperatureunder reflux for 2 hours
customThe solvent is removed under reduced pressure
dissolutionThe residue is dissolved in methanol
customre-evaporated
customThe solid residue is purified by chromatography on reverse phase Baker G18 silica gel available from J.T

Sources & evidence

ORD record: ord-c56b42dd4f524a2cb77c8c68b9f4c7bc
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06022966

Linked notes

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