Dichloromethane → p-Toluenesulfonic acid

(2-tert-Butoxycarbonylamino-ethyl-2-{[tert-butoxycarbonyl-(2-tert-butoxycarbonylaminoethylamino]-methyl}-8-hydroxyoctyl)-carbonic acid tert-butyl ester (2.52 g, 3.82 mmol), p-toluenesulfonyl chloride (1.0 g, 5.2 mmol), triethylamine (1.3 g, 12.8 mmol) and CH2Cl2 (30 ml) were stirred at room temperature with the slow evaporation of solvent. The reaction was monitored by carbon NMR and after 3 days little starting material remained. The reaction volume was made up to 30 ml with CH2Cl2, extracted with water (50 ml×3), dried (MgSO4), filtered and the solvent evaporated to leave a brown residue. This residue was subjected to chromatography on silica gel using CH2Cl2/MeOH (100:5) as eluent. The first compound to elute was unreacted tosyl chloride with an rf=0.95. The title compound eluted with an rf=0.2 and was isolated as a pale yellow viscous oil. Yield (1.20 g, 39%).

1. extractionextracted with water (50 ml×3)
2. dry with materialdried (MgSO4)
3. filtrationfiltered
4. customthe solvent evaporated
5. customto leave a brown residue
6. washThe first compound to elute
7. washThe title compound eluted with an rf=0.2
8. customwas isolated as a pale yellow viscous oil
9. customYield (1.20 g, 39%)

ORD record

ord-5905fdd176ad40b386ca363af93bce2b

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304388B2