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

HRID 34630

反応式

HRID 34630 の反応式
[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]

参加物

6

反応物 3

HCID 7405L-Pyroglutamic AcidHCID 81741-DecanolHCID 10868Dicyclohexylcarbodiimide

生成物 1

HCID 22839298Decyl 5-oxo-L-prolinate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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°.

後処理

  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°

出典と根拠

ORDレコード
ord-a2d6868564ac4e5fa674d173dbe62663
出典データセット
uspto-grants-1988_08
特許番号
US04762851

関連ノート

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