Hydrochloric Acid → HCID 10535993, compound

HRID 1756041Notes

Reaction equation

HRID 1756041 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[C:9](Cl)(=[O:14])[CH2:10][CH:11]([CH3:13])[CH3:12].Cl>[OH-].[Na+]>[C:9]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])(=[O:14])[CH2:10][CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66054Isovaleryl chlorideHCID 145742L-Proline

Product 1

HCID 10535993HCID 10535993, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a well stirred solution of L-proline (1.15 g; 0.01 mole) in 2N aq. NaOH (5 ml), 4N aq. NaOH (2.5 ml) and iso-valeryl chloride (1.4 ml; 0.012 mole) were added simultaneously dropwise maintaining the temperature near 0°-4° C. After 15 minutes, the mixture was acidified (pH 2-3) with 1N HCl and extracted with CHCL3. The combined organic extract was dried using MgSO4, and the solvent was removed. N-iso-valeryl-L-proline was obtained as an oil. Yield 0.85 g, Rf =0.66 (Silica gel, n-C4H9OH-AcOH-H2O, 5:1:2); [α]D20 -129.3° (c 0.6; CHCl3).

Workup

  1. temperaturemaintaining the temperature near 0°-4° C
  2. extractionextracted with CHCL3
  3. extractionThe combined organic extract
  4. customwas dried
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-5b3f0a70d99e4d30b745c0281131704a
Source dataset
uspto-grants-1995_08
Patent number
US05439930

Reaction notes

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