Acetic Acid → HCID 13246942, compound

HRID 2256016Notes

Reaction equation

HRID 2256016 reaction equation
[C:1](OC(=O)C)(=O)[CH3:2].[CH:8]([NH:10][CH2:11][C:12]([OH:14])=[O:13])=[CH2:9].CC(O)=[O:17]>>[C:8]([NH:10][CH:11]([CH:1]=[CH2:2])[C:12]([OH:14])=[O:13])(=[O:17])[CH3:9]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 14162523HCID 14162523, compound

Product 1

HCID 13246942HCID 13246942, compoundYield 55%

Procedure

Acetic anhydride (2.50 g, 24.50 mmol) was added slowly into a cooled (-10° C.) solution of vinyl glycine (2.20 g, 21.78 mmol) in AcOH (100 mL). The mixture was stirred at this temperature (30 min) and then at room temperature (3 h). The solution was concentrated repeatedly from H2O. The residue was dissolved in absolute EtOH (200 mL) and then decolorized (norit, 60° C.), and filtered. The filtrate was concentrated in vacuo, and the residue was triturated with Et2O to give 1.70 g (55%) of the desired product as a low melting yellow solid: 1H NMR (DMSO-d6) δ 1.87 (s, C(O)CH3), 4.75 (dd, J=6.2, 7.5 Hz, α-CH), 5.13-5.27 (m, CH=CH2), 5.84-5.96 (m, CH=CH2), 8.24 (d, J=7.5 Hz, NH).

Workup

  1. customat room temperature
  2. custom(3 h)
  3. concentrationThe solution was concentrated repeatedly from H2O
  4. dissolutionThe residue was dissolved in absolute EtOH (200 mL)
  5. custom(norit, 60° C.)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue was triturated with Et2O

Sources & evidence

ORD record
ord-98eaef2d2f38475ba7f517b9209298d4
Source dataset
uspto-grants-1997_08
Patent number
US05654301

Reaction notes

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