Water → (R)-2-(((Benzyloxy)carbonyl)amino)pent-4-enoic acid

HRID 1392076Notes

Reaction equation

HRID 1392076 reaction equation
[CH2:1]=[CH:2][CH2:3][C@@H:4]([NH2:8])[C:5]([OH:7])=[O:6].C(N(CC)CC)C.O.[CH2:17]([O:24][C:25](ON1C(=O)CCC1=O)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCOCC1>[CH2:17]([O:24][C:25]([NH:8][C@H:4]([CH2:3][CH:2]=[CH2:1])[C:5]([OH:7])=[O:6])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 6992334D-Allylglycine

Product 1

HCID 10243780(R)-2-(((Benzyloxy)carbonyl)amino)pent-4-enoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of D-2-amino-4-pentenoic acid (500 mg) in Dioxane (20 mL) at RT was added triethylamine (1.09 g), water (0.5 mL), and N-(benzyloxycarbonyloxy)succinimide (2.27 g). The reaction mixture was stirred overnight at RT, concentrated in vacuo, diluted with saturated NaHCO3 and extracted with ether (3×). The basic aqueous layer was acidified to pH 2 with 2N HCl and extracted with EtOAc (3×). The combined EtOAc layer was washed with brine, dried (Na2SO4), filtered and concentrated to give a clear viscous oil (1.17 g, quantitative).

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with saturated NaHCO3
  3. extractionextracted with ether (3×)
  4. extractionextracted with EtOAc (3×)
  5. washThe combined EtOAc layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a clear viscous oil (1.17 g, quantitative)

Sources & evidence

ORD record
ord-3c72e5f661ee4609b9b4467a28e05e4c
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

Loading…