Potassium Hydroxide → HCID 131712644, compound

The 5S,6R dimethylester, i.e. (5S,6R)(E,E,Z,Z)-S-(5-hydroxy-1-methoxy-1-oxoeicosa-7,9,11,14-tetraen-6-yl)-L-cysteine methyl ester (0.3 g) was dissolved in methanol (15 mL) and treated with potassium hydroxide (150 mg) in water (1.5 mL) and left at room temperature for 90 min. Water (20 mL) was then added and the bulk of the solvents were removed in vacuo. The aqueous solution resulting from the above treatment was mixed with Dowex 50W ×4 resin (25 mL) [sulfonated polystyrene ion exchange resin in the acid form] and then poured onto a column of the same material (25 mL). The column was then washed with water until neutral and then eluted with aqueous ammonia solution (10%). As soon as the ammonia front was eluting, 150 mL was collected, treated with n-butanol (10 mL) and concentrated at 45° and 20 nm until all the n-butanol and ammonia were removed. The residual aqueous solution was then freeze-dried to yield the (5S,6R) (E,E,Z,Z)-S-(5-hydroxy-1-hydroxy-1-oxoeicosa-7,9,11,14-tetraen-6-yl)-L-cysteine mono ammonium salt as a powder (130 mg).

1. customthe bulk of the solvents were removed in vacuo
2. customThe aqueous solution resulting from the above treatment
3. washThe column was then washed with water until neutral and
4. washthen eluted with aqueous ammonia solution (10%)
5. washAs soon as the ammonia front was eluting
6. custom150 mL was collected
7. additiontreated with n-butanol (10 mL)
8. concentrationconcentrated at 45°
9. custom20 nm until all the n-butanol and ammonia were removed
10. customThe residual aqueous solution was then freeze-dried

ORD record

ord-d2044af0372447ea9bd852941ef3d17a

Source dataset

uspto-grants-1982_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04311645