Water → HCID 21949598, compound

HRID 2215254Notes

Reaction equation

HRID 2215254 reaction equation
[C:1]([NH:6][CH:7]([CH2:11][CH:12]=[CH2:13])[C:8]([OH:10])=O)(=[O:5])[CH:2]([CH3:4])[CH3:3].[C:14](OC(=O)C)(=O)C.O>N1C=CC=CC=1>[C:8]([CH:7]([NH:6][C:1](=[O:5])[CH:2]([CH3:3])[CH3:4])[CH2:11][CH:12]=[CH2:13])(=[O:10])[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 21949603HCID 21949603, compound

Product 1

HCID 21949598HCID 21949598, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

7.77 g of the above synthesized 2-isobutyrylamino-pent-4-enoic acid (41.95 mmol) were dissolved in 36.5 ml of pyridine, treated with 19.83 ml of acetic anhydride (5 eq.), and heated to 100° for 1 h. After cooling, 28.3 ml of water were added and the mixture kept for 20 Min. at 90°. Careful pouring onto crashed ice/HCl, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (silica gel, hexane/AcOEt=1/1) left finally 6.63 g of the title compound as yellowish oil.

Workup

  1. temperatureheated to 100° for 1 h
  2. temperatureAfter cooling
  3. customat 90°
  4. additionCareful pouring
  5. extractionice/HCl, twofold extraction with AcOEt
  6. washwashing with water and brine
  7. dry with materialdrying over magnesium sulfate, and evaporation of the solvents
  8. waitleft finally 6.63 g of the title compound as yellowish oil

Sources & evidence

ORD record
ord-356aae0fe61947479eff81fcacf11851
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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