Hydrochloric Acid → 3-Cyclobutyl-D-alanine

HRID 1977582Notes

Reaction equation

HRID 1977582 reaction equation
COC([NH:5][C@@H:6]([C:12]([OH:14])=[O:13])[CH2:7][CH:8]1[CH2:11][CH2:10][CH2:9]1)=O.Cl.O1C(C)C1>>[CH:8]1([CH2:7][C@H:6]([C:12]([OH:14])=[O:13])[NH2:5])[CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6378Propylene OxideHCID 70072578HCID 70072578, compound

Product 1

HCID 509993233-Cyclobutyl-D-alanine

Procedure

To 1.0 g (5 mmol) of methoxycarbonyl-3-cyclobutyl-D-alanine (Example 2, Step 2) 10 ml of 6M HCl is added and heated to reflux for 3 hours. The solution is evaporated at a pressure of 2.0-2.5 kPa, the residue is dissolved in 5 ml of water and evaporated to dryness and this process is repeated. The traces of water can be removed by azeotropic distillation with ethanol-benzene mixture. The residual oil is dissolved in 10 ml of ethanol and 5 mmol of 1,2-epoxy-propane is added. After cooling the precipitate is filtered off, the solid is washed with diethyl ether and dried.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. customThe solution is evaporated at a pressure of 2.0-2.5 kPa
  4. dissolutionthe residue is dissolved in 5 ml of water
  5. customevaporated to dryness
  6. customThe traces of water can be removed by azeotropic distillation with ethanol-benzene mixture
  7. dissolutionThe residual oil is dissolved in 10 ml of ethanol
  8. temperatureAfter cooling the precipitate
  9. filtrationis filtered off
  10. washthe solid is washed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-d7a4717495f54c99935c535b5260b2d1
Source dataset
uspto-grants-2001_05
Patent number
US06235707B1

Reaction notes

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