Hydrochloric Acid → HCID 57617058, compound

HRID 1360101Notes

Reaction equation

HRID 1360101 reaction equation
C[O:2][C:3](=[O:16])[C@H:4]([CH2:12][CH2:13][CH2:14][CH3:15])[NH:5][C:6](=[O:11])[CH2:7][CH2:8][CH:9]=[CH2:10].[OH-].[Na+].Cl>C1COCC1>[C:6]([NH:5][C@H:4]([C:3]([OH:16])=[O:2])[CH2:12][CH2:13][CH2:14][CH3:15])(=[O:11])[CH2:7][CH2:8][CH:9]=[CH2:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86628750HCID 86628750, compound

Product 1

HCID 57617058HCID 57617058, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Pent-4-enoyl-L-norleucine methyl ester (0.30 g, 1.32 mmol) was dissolved in THF (3 mL) and 1 M NaOH (3 mL) was added at RT. The reaction mixture was stirred for 3 h, poured onto ethyl acetate and 1 M HCl and the layers were separated. The organic layer was washed with water, dried over NaSO4, filtered and concentrated to give N-pent-4-enoyl-L-norleucine (0.25 g, 89% yield): 1H NMR (400 MHz, CD3OD) 8 ppm 5.81 (m, 1H), 5.02 (d, 1H), 4.95 (d, 1H), 4.82 (br s, 1H), 4.27 (m, 1H), 2.32 (br s, 4H), 1.80 (m, 1H), 1.65 (m, 1H), 1.37 (m, 4H), 0.9 (t, 3H).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with water
  3. dry with materialdried over NaSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b84a9e7bb2a54ece855aa36d79ccc157
Source dataset
uspto-grants-2011_02
Patent number
US07879797B2

Reaction notes

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