Diketene → HCID 86682311, compound

HRID 1055243Notes

Reaction equation

HRID 1055243 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.Cl.[CH3:8][O:9][C:10](=[O:15])[C@H:11]([CH2:13][OH:14])[NH2:12].C([O-])(O)=O.[Na+]>C1COCC1>[O:6]=[C:2]([CH3:1])[CH2:3][C:4]([NH:12][C@H:11]([C:10]([O:9][CH3:8])=[O:15])[CH2:13][OH:14])=[O:5]

Participants

5

Reactant 3

HCID 12661DiketeneHCID 516892Sodium BicarbonateHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 86682311HCID 86682311, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.8 g (0.13 mol) of diketene, 20 g L-serine methyl ester hydrochloride (0.13 mol) and 21.6 g (0.26 mol, 2 eq) of NaHCO3 were mixed in 1000 ml of THF at 0° C. Then the ice bath was removed and it was stirred further at room temperature. After 24 h stirring at room temperature, the reaction mixture was filtered and the residue was recrystallized from 100 ml of ethyl acetate. This gave 21.14 g (0.10 mol, 81% yield) as a white solid.

Workup

  1. customThen the ice bath was removed
  2. stirringAfter 24 h stirring at room temperature
  3. filtrationthe reaction mixture was filtered
  4. customthe residue was recrystallized from 100 ml of ethyl acetate

Sources & evidence

ORD record
ord-9a6b879e18c6411daf67d87471779ef3
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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