Hydrochloric Acid → N-[(pent-4-en-1-yloxy)carbonyl]-norleucine

HRID 1360097Notes

Reaction equation

HRID 1360097 reaction equation
C[O:2][C:3](=[O:18])[C@H:4]([CH2:14][CH2:15][CH2:16][CH3:17])[NH:5][C:6]([O:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13])=[O:7].[OH-].[Na+].CCOC(C)=O.Cl>C1COCC1>[CH2:9]([O:8][C:6]([NH:5][C@H:4]([C:3]([OH:18])=[O:2])[CH2:14][CH2:15][CH2:16][CH3:17])=[O:7])[CH2:10][CH2:11][CH:12]=[CH2:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 45378375methyl N-[(pent-4-enyloxy)carbonyl]-norleucinate

Product 1

HCID 45378373N-[(pent-4-en-1-yloxy)carbonyl]-norleucineYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [(4-pentenyloxy)carbonyl]-L-norleucine methyl ester (1.8 g, 7.0 mmol) in THF (5 mL) at RT was added 1M sodium hydroxide solution (5 mL). The reaction mixture was stirred at RT for 3 h. The reaction mixture was then worked up with EtOAc and 1M HCl. The organic layer was separated and washed with H2O, brine, dried over Na2SO4, filtered and concentrated to give [(4-pentenyloxy)carbonyl]-L-norleucine (1.4 g, 82% yield). 1H NMR (500 MHz, CD3OD) ppm: δ 5.82 (m, 1H), 5.05 (d, 1H), 4.98 (d, 1H), 4.86 (brs, 2H), 4.10 (m, 1H), 4.08 (t, 2H), 2.16 (q, 2H), 1.82 (m, 1H), 1.72 (m, 3H), 1.38 (m, 4H), 0.93 (t, 3H).

Workup

  1. customThe organic layer was separated
  2. washwashed with H2O, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0533e41ab36e4f88b266b7b0a35665dd
Source dataset
uspto-grants-2011_02
Patent number
US07879797B2

Reaction notes

Loading…