Methanol → (R)-Methyl 2-amino-3-(4-methoxyphenyl)propanoate

HRID 540378Notes

Reaction equation

HRID 540378 reaction equation
S(=O)(=O)(O)O.[NH2:6][C@H:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:8]([OH:10])=[O:9].[OH-].[Na+].[CH3:22]O>>[NH2:6][C@H:7]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[C:8]([O:10][CH3:22])=[O:9]

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 6950205O-Methyl-D-tyrosine

Product 1

HCID 11241250(R)-Methyl 2-amino-3-(4-methoxyphenyl)propanoateYield 92%

Procedure

20 ml of sulphuric acid are added, dropwise, over a period of 30 minutes, to a solution containing 13 g (66.6 mmol) of (R)-2-amino-3-(4-methoxyphenyl)propionic acid in 150 ml of methanol. After stirring for 24 hours at ambient temperature, the reaction medium is basified to pH 8-9 by introducing 10N sodium hydroxide and a saturated solution of sodium hydrogen carbonate, followed by extraction with dichloromethane. The organic phase is dried over sodium sulphate, filtered and evaporated. 12.8 g in the form of a pale yellow oil are obtained with a yield of 92%.

Workup

  1. extractiona saturated solution of sodium hydrogen carbonate, followed by extraction with dichloromethane
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. custom12.8 g in the form of a pale yellow oil are obtained with a yield of 92%

Sources & evidence

ORD record
ord-0b7657ab421e40888ef06ee7082ff4a2
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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