Water → HCID 21949646, compound

HRID 2215216Notes

Reaction equation

HRID 2215216 reaction equation
[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]([NH:5][CH:6]([CH2:10][CH:11]=[CH2:12])[C:7]([OH:9])=O)=[O:4].[C:15](OC(=O)CC)(=O)[CH2:16]C.O>N1C=CC=CC=1>[CH3:13][C:2]([CH3:1])([CH3:14])[C:3]([NH:5][CH:6]([C:7](=[O:9])[CH2:15][CH3:16])[CH2:10][CH:11]=[CH2:12])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 31263Propionic anhydrideHCID 21949644HCID 21949644, compound

Product 1

HCID 21949646HCID 21949646, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4.27 g of the above synthesized 2-(2,2-dimethyl-propionylamino)-pent-4-enoic acid (21.43 mmol) were dissolved in 13.5 ml of pyridine, treated with 132.81 ml of propionic anhydride (5 eq.), and heated to 100° for 15 h. After cooling, 10.04 ml of water were added and the mixture kept for 45 Min. at 90°. Careful pouring onto crashed ice/HCl, twofold extraction with AcOEt, washing twice with Na2CO3 and water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (silica gel, hexane/AcOEt=8/2) left finally 2.10 g of the title compound as yellowish oil.

Workup

  1. temperatureheated to 100° for 15 h
  2. temperatureAfter cooling
  3. customat 90°
  4. additionCareful pouring
  5. extractionice/HCl, twofold extraction with AcOEt
  6. washwashing twice with Na2CO3 and water
  7. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  8. waitleft finally 2.10 g of the title compound as yellowish oil

Sources & evidence

ORD record
ord-dd61856c05884e8fb761755cd780b2ba
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

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