Benzyl Alcohol → Benzyl L-threoninate

HRID 909609Notes

Reaction equation

HRID 909609 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[C@@H:3]([CH3:5])[OH:4].[CH2:9](O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[NH2:1][C@H:2]([C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[C@@H:3]([CH3:5])[OH:4]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 6288L-ThreonineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 7022318Benzyl L-threoninateYield 28.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

L-threonine 21.2 g (178 mmol) was dissolved in toluene (100 mL), and benzyl alcohol (100 mL, 966 mmol) and p-toluenesulfonic acid monohydrate (35.0 g, 194 mmol) were added, followed by heating to reflux for 17 hours under nitrogen atmosphere. After cooling to room temperature, water (200 mL) was added, followed by washing three times with ethyl acetate (100 mL). To the aqueous layer, a saturated aqueous sodium hydrogencarbonate solution was added, and extraction was carried out three times with ethyl acetate (100 mL). After the organic layer was washed with saturated brine, drying was carried out over anhydrous magnesium sulfate, and the resulting residue was purified using silica gel column chromatography (elution solvent: methanol/methylene chloride=0%-15%) to afford the desired product (10.6 g, yield 28%) as a white solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 17 hours under nitrogen atmosphere
  3. washby washing three times with ethyl acetate (100 mL)
  4. additionTo the aqueous layer, a saturated aqueous sodium hydrogencarbonate solution was added
  5. extractionextraction
  6. washAfter the organic layer was washed with saturated brine
  7. customdrying
  8. customthe resulting residue was purified
  9. washsilica gel column chromatography (elution solvent: methanol/methylene chloride=0%-15%)

Sources & evidence

ORD record
ord-31235e558aca4c1a87bacfac002c4d2a
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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