Hydrochloric Acid → HCID 57539222, compound

HRID 2096924Notes

Reaction equation

HRID 2096924 reaction equation
[NH2:1][C@H:2]([CH2:6][O:7][CH:8]([F:10])[F:9])[C:3]([OH:5])=[O:4].C(=O)(O)[O-].[Na+].[C:16](OC(=O)C)(=[O:18])[CH3:17].Cl>O.O1CCOCC1>[C:16]([NH:1][C@H:2]([CH2:6][O:7][CH:8]([F:10])[F:9])[C:3]([OH:5])=[O:4])(=[O:18])[CH3:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 57539232HCID 57539232, compound

Product 1

HCID 57539222HCID 57539222, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

(2R)-2-Amino-3-(difluoromethoxy)propanoic acid (680 mg, 4.39 mmol) was mixed with sodium bicarbonate (738 mg. 8.78 mmol) and acetic anhydride (491 mg, 4.82 mmol) in water (10 mL) and dioxane (10 mL) at 0° C. to room temperature overnight. The reaction mixture was acidified with 1N HCl to pH 2, concentrated and extracted with ethyl acetate, and concentrated again to give (2R)-2-(Acetylamino)-3-(difluoromethoxy)propanoic acid (580 mg, 82.3%) as a colorless sticky oil. 1H NMR (300 MHz, CDCl3): (ppm) 6.40 (d, 1H), 6.24 (wt, 1H), 4.88 (m, 1H), 4.36 (dd, 1H), 4.22 (dd, 1H), 2.12 (s, 3H).

Workup

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated again

Sources & evidence

ORD record
ord-6edf9d9405cc4879b074c726bc0bca61
Source dataset
uspto-grants-2013_05
Patent number
US08450336B2

Reaction notes

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