Hydrochloric Acid → HCID 22632156, compound

HRID 2416707Notes

Reaction equation

HRID 2416707 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:14][C:15]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:16]=1[CH2:17][CH2:18][C:19]([O:21]C)=[O:20])[CH2:9][C:10]([F:13])([F:12])[F:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>O1CCOCC1>[C:1]([O:5][C:6]([N:8]([CH2:14][C:15]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:16]=1[CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:9][C:10]([F:11])([F:12])[F:13])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22632212HCID 22632212, compound

Product 1

HCID 22632156HCID 22632156, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl 2-[N-(tert-butoxycarbonyl)-N-(2,2,2-trifluoroethyl)aminomethyl]-4-methoxydihydrocinnamate (43.71 g, 108 mmol) in dioxane (200 mL) was added aqueous 1 N NaOH (130 mL, 130 mmol). The cloudy reaction was stirred at RT for 4 h. The resulting a homogeneous solution was neutralized with 1 N HCl (130 mL, 130 mmol) and extracted with ethyl acetate (2×250 mL). The combined organic layers were washed with brine (250 mL), dried (MgSO4), and concentrated to give the title compound (45.01 g, 100%) as a thick clear oil: TLC (95:4:1 CHCl3, MeOH, HOAc) Rf 0.49.

Workup

  1. customThe cloudy reaction
  2. extractionextracted with ethyl acetate (2×250 mL)
  3. washThe combined organic layers were washed with brine (250 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8d46619fb2f040a6ae3386e6b4f2fe4e
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

Loading…