N-Carbethoxyphthalimide → HCID 11139382, compound

HRID 1392082Notes

Reaction equation

HRID 1392082 reaction equation
[CH2:1]=[CH:2][CH2:3][C@H:4]([NH2:8])[C:5]([OH:7])=[O:6].C(N1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24])(OCC)=O>C([O-])([O-])=O.[Na+].[Na+]>[O:19]=[C:18]1[C:17]2[C:16](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15](=[O:24])[N:8]1[C@@H:4]([CH2:3][CH:2]=[CH2:1])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 31187N-CarbethoxyphthalimideHCID 167529s-Allylglycine

Product 1

HCID 11139382HCID 11139382, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

To a solution of L-2-amino-4-pentenoic acid (9.88 g) in an aqueous Na2CO3 (9.11 g, 150 mL) at RT was added N-carboethoxyphthalimide (18.8 g). The reaction mixture was stirred for 6 h at RT, gradually becoming homogeneous. The reaction mixture was transferred to a separatory funnel and extracted with DCM (3×). The basic aqueous layer was made acidic with 2N HCl and extracted with DCM (3×). The combined DCM layer was washed with brine, dried (Na2SO4), filtered and evaporated. The crude product was purified via column chromatography (2% MeOH/DCM) to give a viscous oil (20.0 g), which crystallized upon standing. 1H NMR (300 MHz, CDCl3) δ 2.93-3.11 (m, 2H), 4.97-5.11 (m, 3H), 5.65-5.79 (m, 1H), 7.71-7.75 (m, 2H), 7.83-7.88 (m, 2H). MS APCI-m/z=246 (M+1). LCMS 1.91 min., Method A.

Workup

  1. customThe reaction mixture was transferred to a separatory funnel
  2. extractionextracted with DCM (3×)
  3. extractionextracted with DCM (3×)
  4. washThe combined DCM layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified via column chromatography (2% MeOH/DCM)

Sources & evidence

ORD record
ord-c587b207b07c41f7bf869d299432b053
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

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