Chloroform → chloroform methanol water NH4OH

DMRIE-Ox (300 mg) was dissolved in 7 mL chloroform and washed with 3 mL 1N HCl. The organic phase was dried with MgSO4, then filtered into a reaction vessel. The solution was placed in an ice-water bath and N-hydrosuccinimide (82 mg) then dicyclohexylcarbodiimide (1.3 mL of a 0.5 M solution in dichloromethane) were added and the reaction was allowed to stir with warming for 8 hours. At this time propyl amine (40 mg) was added as a neat liquid and the reaction allowed to stir at room temperature overnight. The reaction was filtered, then evaporated. Chromatography of the filtrate residue through silica gel with CHCl3:MeOH:NH4OH:H2O (90:10:0.25:0.25) afforded pure product.

1. washwashed with 3 mL 1N HCl
2. dry with materialThe organic phase was dried with MgSO4
3. filtrationfiltered into a reaction vessel
4. customThe solution was placed in an ice-water bath
5. additionN-hydrosuccinimide (82 mg) then dicyclohexylcarbodiimide (1.3 mL of a 0.5 M solution in dichloromethane) were added
6. temperaturewith warming for 8 hours
7. additionAt this time propyl amine (40 mg) was added as a neat liquid
8. stirringto stir at room temperature overnight
9. filtrationThe reaction was filtered
10. customevaporated

ORD record

ord-dc1e615057304224a797f221d68e1d21

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541628B2