Water → HCID 101855330, compound

HRID 1988294Notes

Reaction equation

HRID 1988294 reaction equation
[NH:1]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[CH2:19](I)[CH3:20].[H-].[Na+].O>C1COCC1>[C:9]([N:1]([CH2:19][CH3:20])[C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 726987N-Carbobenzoxy-L-valine

Product 1

HCID 101855330HCID 101855330, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of Z-Val-OH (50 g) in THF (500 ml), ethyl iodide (127.3 ml, 1592 mmol) was added under cooling with ice and then sodium hydride (60% in oil) (23.88 g, 597 mmol) was added slowly, followed by stirring at 60° C. for 12 hours. The reaction mixture was mixed with water and washed with ether. The thus obtained aqueous layer was rendered acidic by the addition of dilute hydrochloric acid and extracted with ethyl acetate. The resultant was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated to remove the solvent under reduced pressure. The thus obtained residue was subjected to silica gel column chromatography (H:EA:AcOH=100:50:1), giving Z-N-Et-Val-OH (V2) (29.29 g, 53%).

Workup

  1. temperatureunder cooling with ice
  2. washwashed with ether
  3. additionThe thus obtained aqueous layer was rendered acidic by the addition of dilute hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. washThe resultant was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-46fae96b9cd945809303e797414a63b3
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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