Sodium Carbonate → VEL-0230

HRID 732264Notes

Reaction equation

HRID 732264 reaction equation
[CH2:1]([O:5][CH2:6][C@@H:7]([NH:12][C:13]([C@H:15]1[O:17][C@@H:16]1[C:18]([O:20]CC)=[O:19])=[O:14])[CH2:8][CH:9]([CH3:11])[CH3:10])[CH:2]([CH3:4])[CH3:3].C(=O)([O-])[O-].[Na+:27].[Na+]>C(O)C.O>[CH2:1]([O:5][CH2:6][C@@H:7]([NH:12][C:13]([C@H:15]1[O:17][C@@H:16]1[C:18]([O-:20])=[O:19])=[O:14])[CH2:8][CH:9]([CH3:11])[CH3:10])[CH:2]([CH3:3])[CH3:4].[Na+:27]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 9948800HCID 9948800, compound

Product 1

HCID 25102841VEL-0230Yield 148.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Crude ethyl (2S,3S)-3-[[(1S)-1-isobutoxymethyl-3-methylbutyl]carbamoyl]oxirane-2-carboxylate (15.29 g) synthesized according to the process (acid chloride method) similar to that described in Patent reference 1 was dissolved in ethanol (24 mL). While the solution was stirred at room temperature, sodium carbonate (2.44 g) dissolved in water (24 mL) was dropped. After the solution was stirred at room temperature for 1 hour, it was further stirred at 90° C. to 95° C. for 2 hours. The solvent was distilled off under reduced pressure, and water (50 mL) was added to the residue. The obtained solution was washed with two portions of ethyl acetate (50 mL), and water was distilled off under reduced pressure. Acetone (400 mL) was dropped to the residue, and the obtained solution was stirred overnight at room temperature. The precipitated crystalline product was collected by filtration, washed with a mixture of 3% water-acetone (30 mL), washed again with acetone (30 mL), and dried in air to obtain white solid sodium (2S,3S)-3-[[(1S)-1-isobutoxymethyl-3-methylbutyl]carbamoyl]oxirane-2-carboxylate (10.55 g, 70.3%). The NMR data of the solid product were the same as those in Example 9.

Workup

  1. additionwas dropped
  2. stirringAfter the solution was stirred at room temperature for 1 hour
  3. stirringit was further stirred at 90° C. to 95° C. for 2 hours
  4. distillationThe solvent was distilled off under reduced pressure, and water (50 mL)
  5. additionwas added to the residue
  6. washThe obtained solution was washed with two portions of ethyl acetate (50 mL), and water
  7. distillationwas distilled off under reduced pressure
  8. additionAcetone (400 mL) was dropped to the residue
  9. stirringthe obtained solution was stirred overnight at room temperature
  10. filtrationThe precipitated crystalline product was collected by filtration
  11. washwashed with a mixture of 3% water-acetone (30 mL)
  12. washwashed again with acetone (30 mL)
  13. customdried in air

Sources & evidence

ORD record
ord-d4027e8594c248c0ae9bfe01a96422d9
Source dataset
uspto-grants-2009_09
Patent number
US07585988B2

Reaction notes

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