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

HRID 34630

Reaction equation

HRID 34630 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 dichloromethane 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 dichloromethane 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-a2d6868564ac4e5fa674d173dbe62663
Source dataset
uspto-grants-1988_08
Patent number
US04762851

Linked notes

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