Water → HCID 70363053, compound

HRID 2165750Notes

Reaction equation

HRID 2165750 reaction equation
[CH3:1][O:2][C:3](=[O:9])[C@@H:4]1[CH2:8][CH2:7][CH2:6][NH:5]1.O.[C:11]([O-:14])(O)=O.[Na+].[CH2:16]1[CH2:20]O[CH2:18][CH2:17]1>>[CH3:1][O:2][C:3](=[O:9])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:11](=[O:14])[CH2:18][CH2:17][CH2:16][CH2:20][CH2:20][CH2:16][CH2:17][CH2:18][CH2:20][CH2:16][CH2:17]/[CH:18]=[CH:20]\[CH2:16][CH2:17][CH2:18][CH2:6][CH2:7][CH2:8][CH2:4][CH3:3]

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 853477Methyl L-prolinate

Product 1

HCID 70363053HCID 70363053, compound

Procedure

In methylene chloride (10 ml) was dissolved erucic acid (2 g). To the solution was added dropwise oxalyl chloride (1.1 ml), and the mixture was refluxed for one hour under heating, followed by concentration to give acid chloride. The acid chloride was stirred, together with L-proline methyl ester (980 mg), in THF (15 ml)-water (1 ml) in the presence of NaHCO3 (800 mg) at room temperature for 15 hours. The solvent was concentrated. To the residue was then added water, and the mixture was subjected to extraction with methylene chloride. The extract was dried and concentrated, followed by purification by means of a silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain a colorless oily product [1.09 g (yield 41%)].

Workup

  1. concentrationThe solvent was concentrated
  2. extractionadded water, and the mixture was subjected to extraction with methylene chloride
  3. customThe extract was dried
  4. concentrationconcentrated
  5. customfollowed by purification by means of a silica gel column chromatography (hexane:ethyl acetate=3:1)
  6. customto obtain a colorless oily product [1.09 g (yield 41%)]

Sources & evidence

ORD record
ord-757cfc4e2a3747278b5f1322b5d29233
Source dataset
uspto-grants-1990_07
Patent number
US04940730

Reaction notes

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