Hydrochloric Acid → (Methoxycarbonyl)-L-threonine

HRID 923388Notes

Reaction equation

HRID 923388 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[C@@H:3]([CH3:5])[OH:4].C(=O)(O)[O-].[Na+].Cl[C:15]([O:17][CH3:18])=[O:16].Cl>C(OCC)C.O>[OH:4][C@H:3]([CH3:5])[C@H:2]([NH:1][C:15]([O:17][CH3:18])=[O:16])[C:6]([OH:8])=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6288L-ThreonineHCID 6586Methyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 28377863(Methoxycarbonyl)-L-threonineYield 16.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

L-Threonine (0.50 g, 4.2 mmol) and sodium bicarbonate (1.13 g, 13.4 mmol) were dissolved into water (20 mL) then cooled in an ice bath. Methyl chloroformate (0.36 mL, 4.62 mmol) was dissolved in diethyl ether (2 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 0.12 g 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-2a9d2329f7ca48d2907ddae2a791bb5f
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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