Water → (2E,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-2-hexenoic acid

LiOH (2.95 g, 123 mmol) was added to a solution of methyl (2E,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-2-hexenoate (6 g, 24.66 mmol) in THF (50 mL), MeOH (10.00 mL), and water (50.0 mL). The reaction was stirred overnight at RT. After 18.5 h, the reaction mixture was concentrated under reduced pressure to remove the THF and MeOH. Water (40 mL) was added, and aqueous mixture was adjusted to pH=3 with 6 M aq. HCl, as measured by pH paper. EtOAc (80 mL) was added, the layers were separated, and the aqueous layer was extracted with EtOAc (2×40 mL). The combined organic layers were dried over Na2SO4, concentrated under reduced pressure, and dried under high vacuum, giving 6.09 g of the title compound. LC-MS m/z 230 (M+H)+, 0.77 min (ret time).

1. waitAfter 18.5 h
2. concentrationthe reaction mixture was concentrated under reduced pressure
3. customto remove the THF and MeOH
4. additionWater (40 mL) was added
5. additionEtOAc (80 mL) was added
6. customthe layers were separated
7. extractionthe aqueous layer was extracted with EtOAc (2×40 mL)
8. dry with materialThe combined organic layers were dried over Na2SO4
9. concentrationconcentrated under reduced pressure
10. customdried under high vacuum

ORD record

ord-fdc1cd8198524bada9faa051c39a4d9b

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187461B2