Hydrochloric Acid → HCID 69904994, compound

HRID 987142Notes

Reaction equation

HRID 987142 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][O:12][C:13]2[CH:30]=[CH:29][C:16]([CH2:17][C@@H:18]([C:25]([O:27]C)=[O:26])[NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])=[CH:15][CH:14]=2)=[CH:6][CH:5]=1)[CH3:2].O.[OH-].[Li+].Cl>O1CCOCC1.O>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:17][C@@H:18]([C:25]([OH:27])=[O:26])[NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])=[CH:29][CH:30]=2)=[CH:8][CH:9]=1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 69905945HCID 69905945, compound

Product 1

HCID 69904994HCID 69904994, compoundYield 102.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl O-[2-(4-ethoxyphenyl)ethyl]-N-isobutyryltyrosinate (0.25 g, 0.61 mmol) was dissolved in dioxane (4 ml). Lithium hydroxide monohydrate (0.1 g, 2.38 mmol) in water (4 ml) was added. The mixture was stirred overnight and then acidified with 1M hydrochloric acid, pH ˜3-4. Dioxane was removed by evaporation in vacuum. The residue was diluted with water and then extracted with dichloromethane. The organic phase was washed with brine and dried with sodium sulfate. The solvent was then evaporated. 0.25 g desired product was obtained, yield 100%.

Workup

  1. customDioxane was removed by evaporation in vacuum
  2. additionThe residue was diluted with water
  3. extractionextracted with dichloromethane
  4. washThe organic phase was washed with brine
  5. dry with materialdried with sodium sulfate
  6. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-673f97f6f81847cd8e07ac35f895d4dd
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

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