Lithium hydroxide, monohydrate → HCID 44221525, compound

HRID 1879248Notes

Reaction equation

HRID 1879248 reaction equation
O.[OH-].[Li+].[F:4][C:5]([F:21])([CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20])[CH2:6][NH:7][C@H:8]([C:12]([O:14]C)=[O:13])[CH:9]([CH3:11])[CH3:10]>C1COCC1.O>[F:4][C:5]([F:21])([CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20])[CH2:6][NH:7][C@H:8]([C:12]([OH:14])=[O:13])[CH:9]([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86637107HCID 86637107, compound

Product 1

HCID 44221525HCID 44221525, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Lithium hydroxide monohydrate (6 eq.) was added to a stirred mixture of methyl N-(2,2-difluorohept-6-en-1-yl)-L-valinate 73 in THF and water (2/1 v/v, 0.013 M) and the mixture was stirred at 60° C. After 1 h, it was cooled to RT and THF was evaporated under reduced pressure. Aqueous 1N HCl was added until pH=5, and the aq. phase was extracted with EtOAc. Drying over Na2SO4, filtration and evaporation under reduced pressure afforded the title compound that was used in the following step without further purification. MS (ES+) m/z 250 (M+H)+.

Workup

  1. temperatureit was cooled to RT
  2. customTHF was evaporated under reduced pressure
  3. additionAqueous 1N HCl was added until pH=5
  4. extractionthe aq. phase was extracted with EtOAc
  5. dry with materialDrying over Na2SO4, filtration and evaporation under reduced pressure

Sources & evidence

ORD record
ord-2cb4d6275b294b3795020ac1472258f8
Source dataset
uspto-grants-2012_11
Patent number
US08314062B2

Reaction notes

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