L-Pyroglutamic Acid → Decyl 5-oxo-L-prolinate

HRID 1073495Notes

Reaction equation

HRID 1073495 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=[O:8].[CH2:10](O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CN(C)C1C=CN=CC=1>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:8]

Participants

6

Reactant 3

HCID 7405L-Pyroglutamic AcidHCID 81741-DecanolHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 22839298Decyl 5-oxo-L-prolinate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To an ice cold suspension of pyroglutamic acid (1.3 g) and n-decanol (1.6 g) in dichloromethane (50 ml), dicyclohexylcarbodiimide (2.1 g) and 4-dimethylaminopyridine (0.1 g) were added. After stirring at ice bath temperature for 2 hours, the cooling bath was removed and the mixture was stirred at room temperature overnight. The michloromethane was evaporated off. The residue was taken in ether and filtered. The filtrate was washed with 1N HCl, water, aqueous bicarbonate and water. It was then dried over Na2SO4 and evaporated. The residue weighed 2.75 g. It was chromatographed over silica gel. The pure decyl ester was eluted with ethylacetate-chloroform (1:4), 2.3 g m.p. 34°-35°.

Workup

  1. additionwere added
  2. customthe cooling bath was removed
  3. stirringthe mixture was stirred at room temperature overnight
  4. customThe michloromethane was evaporated off
  5. filtrationfiltered
  6. washThe filtrate was washed with 1N HCl, water, aqueous bicarbonate and water
  7. dry with materialIt was then dried over Na2SO4
  8. customevaporated
  9. customIt was chromatographed over silica gel
  10. washThe pure decyl ester was eluted with ethylacetate-chloroform (1:4), 2.3 g m.p. 34°-35°

Sources & evidence

ORD record
ord-93cd998cdc6b4772b0440b3c0e20b6a3
Source dataset
uspto-grants-1990_11
Patent number
US04970206

Reaction notes

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