Palmitoyl Serinol → HCID 42606463, compound

Temperature

0 °C

1.0 g. of the resulted 2-(hexadecanoylamino)propane-1,3-diol were transferred to a three necks round bottom flask equipped with a dropping funnel, a cooling bath, and a magnetic stirrer, under an air stream. The compound was dissolved in 200 ml dry THF and the solution wad cooled to 0° C. 1.2 g of LiAlH4 were added in small portions with strong stirring during 1 hour and then the mixture was left to react for another 2 hours at 0° C. The cooling bath was removed and the reaction was left to stir overnight. The next day, 2 ml of ethyl acetate followed by 10 ml of methanol and 10 ml of HCl 1N, were added very slowly and the solution was evaporated to approximately 20 ml. The mixture was transferred to a separatory funnel and 100 ml water, 100 ml dichloromethane and 50 ml methanol were added. Following shaking, the lower phase was collected and the upper, acidic-aqueous-methanolic phase was extracted twice with 50 ml CH2Cl2:MeOH, 3:1. The combined organic phases were washed with 100 ml HCl 0.1 N and then with 100 ml H2O, dried for 2 hours over MgSO4, filtered and evaporated to dryness. The resulted product was crystallized from ethanol: H2O. Yield: 0.5 g.

1. customequipped with a dropping funnel, a cooling bath, and a magnetic stirrer, under an air stream
2. waitthe mixture was left
3. customto react for another 2 hours at 0° C
4. customThe cooling bath was removed
5. waitthe reaction was left
6. stirringto stir overnight
7. additionwere added very slowly
8. customthe solution was evaporated to approximately 20 ml
9. customThe mixture was transferred to a separatory funnel
10. addition100 ml water, 100 ml dichloromethane and 50 ml methanol were added
11. stirringFollowing shaking
12. customthe lower phase was collected
13. extractionthe upper, acidic-aqueous-methanolic phase was extracted twice with 50 ml CH2Cl2
14. washThe combined organic phases were washed with 100 ml HCl 0.1 N
15. dry with materialwith 100 ml H2O, dried for 2 hours over MgSO4
16. filtrationfiltered
17. customevaporated to dryness
18. customThe resulted product was crystallized from ethanol

ORD record

ord-beee0451ec064a2d81e97eac1a7b2e3c

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962891B2