Water → (2S)-2-{[(Benzyloxy)carbonyl]amino}pent-4-enoic acid

HRID 1392072Notes

Reaction equation

HRID 1392072 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 167529s-Allylglycine

Product 1

HCID 11776816(2S)-2-{[(Benzyloxy)carbonyl]amino}pent-4-enoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of L-2-amino-4-pentenoic acid (2.0 g) in Dioxane (80 mL) at RT was added triethylamine (4.3 g), water (2.0 mL), and N-(benzyloxycarbonyloxy)succinimide (9.1 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 evaporated, then concentrated from Toluene (2×) to give a viscous oil (4.51 g, quantitative). 1H NMR (300 MHz, DMSO-d6) δ 2.31-2.50 (m, 2H), 4.00-4.06 (m, 1H), 5.03 (s, 2H), 5.05-5.12 (m, 2H), 5.71-5.84 (m, 1H), 7.35 (m, 5H), 7.53 (d, 1H), 12.57 (bs, 1H). MS APCI, m/z=250 (M+1). LC/MS 2.30 min., Method A.

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. customevaporated
  9. concentrationconcentrated from Toluene (2×)
  10. customto give a viscous oil (4.51 g, quantitative)
  11. customLC/MS 2.30 min., Method A

Sources & evidence

ORD record
ord-1fc3ec4882b642c09b24723f2d386789
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

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