Hydrochloric Acid → HCID 59540396, compound

HRID 923393Notes

Reaction equation

HRID 923393 reaction equation
[NH2:1][C@@H:2]([C:6]([CH3:9])([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4].C(=O)(O)[O-].[Na+].[CH3:15][O:16][CH2:17][C:18](Cl)=[O:19].Cl>C(OCC)C.O>[CH3:15][O:16][CH2:17][C:18]([NH:1][C@@H:2]([C:6]([CH3:9])([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4])=[O:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 96623Methoxyacetyl chlorideHCID 164608L-tert-LeucineHCID 516892Sodium Bicarbonate

Product 1

HCID 59540396HCID 59540396, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

(S)-2-amino-3,3-dimethylbutanoic acid (0.50 g, 3.8 mmol) and sodium bicarbonate (0.80 g, 9.5 mmol) were dissolved into water (20 mL) then cooled in an ice bath. Methoxyacetyl chloride (0.38 mL, 4.2 mmol) was dissolved in diethyl ether (5 mL) and added dropwise with vigorous stirring. The solution was stirred at ambient temperature for 5 hours then adjusted to pH 3 with concentrated hydrochloric acid and extracted into ethyl acetate. The organic solution was dried over sodium sulfate, filtered, and concentrated to give 0.16 g (21%) of the title compound as a waxy solid.

Workup

  1. temperaturethen cooled in an ice bath
  2. additionadded dropwise with vigorous stirring
  3. extractionextracted into ethyl acetate
  4. dry with materialThe organic solution was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4b99f4d8edc647209e5e44717ca47714
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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