Diisopropylethylamine → HCID 131725286, compound
Reaction equation
Cl.[OH:2][CH:3]1[O:11][C@H:10]([CH2:12][OH:13])[C@@H:8]([OH:9])[C@H:6]([OH:7])[C@H:4]1[NH2:5].C(N(C(C)C)CC)(C)C.[I:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1>CN(C=O)C>[I:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][C:3]2([O:11][C@H:10]([CH2:12][OH:13])[C@@H:8]([OH:9])[C@H:6]([OH:7])[C@H:4]2[NH2:5])[OH:2])=[CH:26][CH:25]=1Participants
Procedure
Thus, a slurry of glucosamine hydrochloride (0.7 g) and diisopropylethylamine (0.6 mL) in DMF (2.0 mL) was stirred at 80° C. for 30 minutes. A solution of 4-iodobenzylbromide (0.4 g) in DMF (2 mL) was added to the reaction mixture, and the resulting mixture stirred for 18 hours. After the reaction mixture was cooled to room temperature, the precipitated solid was removed from the supernatant by decanting. Volatiles were removed from the supernatant, and the resulting residue was separated on a si-gel column using 10% aqueous MeCN as the eluent to yield 50 mg of pure 4-iodobenzyl glucosamine (compound TP012 in the scheme above). The purity of 4-iodobenzyl bromide, which can vary greatly from batch to batch if obtained from commercial suppliers, will affect the yields of this reaction accordingly. The compound 4-Iodobenzyl galactosamine can be prepared using a similar reaction scheme, starting from galactosamine hydrochloride and iodobenzyl bromide.
Workup
- customthe precipitated solid was removed from the supernatant
- customby decanting
- customVolatiles were removed from the supernatant
- customthe resulting residue was separated on a si-gel column
Sources & evidence
- ORD record
- ord-41e3e648ae054530ab1057b9c50f253f
- Source dataset
- uspto-grants-2006_02
- Patent number
- US07001888B2
Reaction notes
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