Cyanogen Bromide → HCID 9995821, compound

5-(Acetylamino)-4-amino-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid (3 g, 10.35 mmol) was suspended in methanol (37.5 ml) and sodium acetate (1.89 g, 23.1 mmol) was added, causing a "caking" of the suspension and making stirring difficult. To this at 21° C. with exclusion of moisture was added a solution of cyanogen bromide (1.14 g, 10.8 mmol) in methanol (150 ml), in a dropwise manner. Stirring gradually became easier, until a readily stirrable suspension was obtained. Addition was complete in 3.5 hr. The mixture was then stirred at 21° C. with exclusion of moisture for 44 hr. The small amount of remaining solid was filtered off and solvent evaporated in vacuo to an orange-brown foam. The foam was taken up in methanol (125 ml) and with rapid stirring at 21° C. was treated dropwise with propan-2-ol (130 ml). The precipitate was filtered off, washed with iPrOH:MeOH 3:2, and combined filtrate and washings evaporated to give the title compound as a pale yellow foam (3.48 g).

1. stirringStirring gradually
2. customwas obtained
3. additionAddition
4. stirringThe mixture was then stirred at 21° C. with exclusion of moisture for 44 hr
5. filtrationwas filtered off
6. customsolvent evaporated in vacuo to an orange-brown foam
7. stirringwith rapid stirring at 21° C.
8. additionwas treated dropwise with propan-2-ol (130 ml)
9. filtrationThe precipitate was filtered off
10. washwashed with iPrOH:MeOH 3:2
11. customevaporated

ORD record

ord-1bd2d4b451024932bb3c36f34d0cd157

Source dataset

uspto-grants-1997_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05639786