Dimethylformamide → methyl N-[(pent-4-enyloxy)carbonyl]-norleucinate

HRID 1095285Notes

Reaction equation

HRID 1095285 reaction equation
[CH2:1]=[CH:2][CH2:3][CH:4]([OH:6])C.[C:7](N1C=CN=C1)(N1C=CN=C1)=[O:8].Cl.[CH3:20][O:21][C:22](=[O:29])[C@H:23]([CH2:25][CH2:26][CH2:27][CH3:28])[NH2:24].[CH3:30]N(C=O)C>C(OCC)C>[CH2:4]([O:6][C:7]([NH:24][C@H:23]([C:22]([O:21][CH3:20])=[O:29])[CH2:25][CH2:26][CH2:27][CH3:28])=[O:8])[CH2:3][CH2:2][CH:1]=[CH2:30]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 122474-Penten-2-OLHCID 682631,1'-CarbonyldiimidazoleHCID 14039065methyl (2S)-2-aminohexanoate hydrochloride

Product 1

HCID 45378375methyl N-[(pent-4-enyloxy)carbonyl]-norleucinateYield 74%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1-penten-4-ol (0.95 g, 11.0 mmol) in DMF (15 mL) at 0° C. was added carbonyldiimidazole (1.79 g, 11.0 mmol). The reaction mixture was warmed to RT and stirred for 30 minutes. L-norleucine methyl ester hydrochloride (2.0 g, 11.0 mmol) was then added, the reaction mixture was heated to 50° C. and stirred for 15 minutes. Upon cooling, the reaction mixture was diluted with ethyl ether and washed twice with water. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography (gradient elution 10 to 90% EtOAc in hexanes) to afford 2.1 g (74%) methyl N-[(pent-4-en-1-yloxy)carbonyl]-L-norleucinate as a clear oil.

Workup

  1. temperaturethe reaction mixture was heated to 50° C.
  2. stirringstirred for 15 minutes
  3. temperatureUpon cooling
  4. washwashed twice with water
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography (gradient elution 10 to 90% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9969c7d03398422d9ea816cf366bcd53
Source dataset
uspto-grants-2012_03
Patent number
US08138164B2

Reaction notes

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