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Glycolic Acid → 1,3-Diethyl 2-[(2-hydroxyacetyl)amino]propanedioate

HRID 1639166
ノート
印刷プレビュー

反応式

HRID 1639166 の反応式
Cl.[NH2:2][CH:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:14](O)(=[O:17])[CH2:15][OH:16].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O.C(N(CC)CC)C>[OH:17][CH2:14][C:15]([NH:2][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:16]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 757Glycolic AcidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)

生成物 1

HCID 150963891,3-Diethyl 2-[(2-hydroxyacetyl)amino]propanedioate収率 62.7%

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 8471Triethylamine溶媒

実験手順

To a solution of diethyl 2-aminomalonate hydrochloride (4.2 g) and glycolic acid (1.6 g) in dimethylformamide is added triethylamine (2.12 g), and to the mixture are added 1-hydroxybenzotriazole (2.7 g) and N,N'-dicyclohexylcarbodiimide (4.33 g) with stirring under ice cooling. The mixture is reacted at 0° to 5° C. for 2 hours and further reacted at room temperature for 15 hours. The reaction mixture is concentrated under reduced pressure, and to the residue is added ethyl acetate, and the undissolved substance is filtered off. The filtrate is washed with aqueous sodium carbonate solution, dried and then the solvent is distilled off. The residue is purified by silica gel column chromatography [solvent: chloroform-ethyl acetate (2:1)] to give diethyl 2-[(hydroxyacetyl)amino]malonate (2.9 g), m.p. 74°-74.5° C.

後処理

  1. customThe mixture is reacted at 0° to 5° C. for 2 hours
  2. customfurther reacted at room temperature for 15 hours
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. additionto the residue is added ethyl acetate
  5. filtrationthe undissolved substance is filtered off
  6. washThe filtrate is washed with aqueous sodium carbonate solution
  7. customdried
  8. distillationthe solvent is distilled off
  9. customThe residue is purified by silica gel column chromatography [solvent: chloroform-ethyl acetate (2:1)]

出典と根拠

ORDレコード
ord-e3aa62b4d44a4aa38f564b34d11c3aed
出典データセット
uspto-grants-1989_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04882447

反応ノート

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