Chloride → HCID 10900461, compound

HRID 1719468Notes

Reaction equation

HRID 1719468 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[C:11](=[O:14])(O)[O-:12].[Na+].[Cl-].O1C[CH2:20][CH2:19][CH2:18]1>O.C(OC(=O)C)C>[CH2:20]([O:12][C:11]([NH:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])=[O:14])[CH:19]=[CH2:18]

Participants

7

Reactant 4

HCID 312ChlorideHCID 8028TetrahydrofuranHCID 33032L-Glutamic AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 10900461HCID 10900461, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
4 °C

Procedure

A solution of L-glutamic acid (6.58 g) in tetrahydrofuran (80 ml) and water (80 ml) containing sodium bicarbonate (11.36 g) is cooled to 4° C. and stirred while adding allykoxycarbonyl chloride (4.25 ml) dropwise during 45 minutes. The mixture is then stirred overnight at room temperature and then diluted with ethylacetate (100 ml). The aqueous phase is separated, acidified with mineral acid and extracted with ethylacetate. The extract is washed with brine, dried and evaporated to give N-allyloxycarbonyl-L-glutamic acid, 8.9 g.

Workup

  1. stirringThe mixture is then stirred overnight at room temperature
  2. customThe aqueous phase is separated
  3. extractionextracted with ethylacetate
  4. washThe extract is washed with brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-743015cc507541329d9186dd65d3ba07
Source dataset
uspto-grants-1985_09
Patent number
US04540579

Reaction notes

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