Citric Acid → 2-Amino-3-(3-difluoromethoxy-phenyl)-propionic acid ethyl ester

HRID 1524879Notes

Reaction equation

HRID 1524879 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH:5]([N:17]=C(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH:14]([F:16])[F:15])[CH:8]=1)[CH3:2].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH2:1]([O:3][C:4](=[O:31])[CH:5]([NH2:17])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH:14]([F:16])[F:15])[CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 311Citric AcidHCID 867279142-(Benzhydrylidene-amino)-3-(3-difluoromethoxy-phenyl)-propionic acid ethyl ester

Product 1

HCID 666741652-Amino-3-(3-difluoromethoxy-phenyl)-propionic acid ethyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 175 Part A (700 mg, 1.65 mmol) was placed in a flask and dissolved in THF (30 mL). 30% (w/v) Citric acid (aqueous solution, 30 mL) was added and the reaction was stirred at rt for 72 h. The solution was extracted with diethyl ether (50 mL), and the aqueous layer was adjusted to a pH 6 using a saturated NaHCO3 solution. The aqueous solution was extracted with dichloromethane, washed with brine, dried over MgSO4, filtered and evaporated to yield 420 mg (97% yield) of a clear glass. MS 260 (M+H)+.

Workup

  1. extractionThe solution was extracted with diethyl ether (50 mL)
  2. extractionThe aqueous solution was extracted with dichloromethane
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-7c5e9d50501f465d80630c8635ba8254
Source dataset
uspto-grants-2015_07
Patent number
US09079860B2

Reaction notes

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