Water → HCID 11435600, compound

HRID 1374445Notes

Reaction equation

HRID 1374445 reaction equation
[NH2:1][C@@H:2]([CH3:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].Cl[C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11].C(N(C(C)C)CC)(C)C.O>C1COCC1>[CH2:13]([O:12][C:10]([NH:1][C@@H:2]([CH3:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5])=[O:11])[CH:14]=[CH2:15]

Participants

6

Reactant 4

HCID 962WaterHCID 18052Allyl chloroformateHCID 81531DiisopropylethylamineHCID 9118386Methyl (3S)-3-aminobutanoate

Product 1

HCID 11435600HCID 11435600, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (3S)-3-aminobutanoate (1.47 g, 12.5 mmol) in THF (30 ml) were added at 0° C. allyl chloroformate (1.60 ml, 15.1 mmol) and diisopropylethylamine (2.62 ml, 15.0 mmol), and the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was poured into water and extracted twice with ethylacetate. The organic layer was washed with a saturated aqueous sodium chloride solution, was dried over magnesium sulfate and the organic solvent was removed under reduced pressure. The residue was purified by silica gel (25 g) chromatography to give methyl (3S)-3-{[(allyloxy)carbonyl]amino}butanoate (2.06 g, 81%).

Workup

  1. extractionextracted twice with ethylacetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialwas dried over magnesium sulfate
  4. customthe organic solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel (25 g) chromatography

Sources & evidence

ORD record
ord-0b850249c58948a6b09c13636a15a08a
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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