Pyridine → HCID 69429312, compound

HRID 2186897Notes

Reaction equation

HRID 2186897 reaction equation
[C:1]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:5])[C@H:2]([CH3:4])[OH:3].N1C=CC=CC=1.Cl[C:21]([O:23][CH2:24][Cl:25])=[O:22]>C(OCC)C>[C:21](=[O:22])([O:23][CH2:24][Cl:25])[O:3][C@H:2]([C:1]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62754Chloromethyl chloroformateHCID 11052238benzyl (2S)-2-hydroxypropanoate

Product 1

HCID 69429312HCID 69429312, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of benzyl (S)-lactate (30.6 g), pyridine (13.4 g) and diethyl ether (300 ml), a solution of chloromethyl chloroformate (21.9 g) in diethyl ether (100 ml) was added dropwise under ice cooling over the period of 30 minutes. After stirring at room temperature for 5 hours, the resulting solid was removed off by filtration. The filtrate was concentrated under reduced pressure and the residue was dissolved in ethyl acetate (200 ml). The solution was washed with water (100 ml×2) and a saturated sodium chloride aqueous solution (100 ml). After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain [(1S)-1-(benzyloxycarbonyl)ethyl] chloromethyl carbonate (45.0 g) as a colorless liquid.

Workup

  1. customthe resulting solid was removed off by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate (200 ml)
  4. washThe solution was washed with water (100 ml×2)
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d90782ca9c34437b91b8256e8219ab38
Source dataset
uspto-grants-2002_06
Patent number
US06407129B1

Reaction notes

Loading…