Triethylamine → Diethyl 2-[[N-(chloroacetyl)glycyl]amino]malonate

HRID 477204ノート

反応式

HRID 477204 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(N(CC)CC)C.[Cl:21][CH2:22][C:23]([NH:25][CH2:26][C:27](O)=[O:28])=[O:24].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[Cl:21][CH2:22][C:23]([NH:25][CH2:26][C:27]([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:28])=[O:24]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 233485N-ChloroacetylglycineHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)

生成物 1

HCID 15053734Diethyl 2-[[N-(chloroacetyl)glycyl]amino]malonate収率 83.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of diethyl 2-aminomalonate hydrochloride (4.2 g) in tetrahydrofuran are added triethylamine (2.1 g) and N-(chloroacetyl)glycine (3.0 g), and the mixture is cooled to 0° to 5° C. To the mixture is further added N,N'-dicyclohexylcarbodiimide (4.3 g), and the mixture is stirred at the same temperature for 2 hours and then allowed to stand at room temperature overnight. Insoluble substance is filtered off from the reaction mixture, and the filtrate is concentrated under reduced pressure. To the residue is added ethyl acetate, and the insoluble substance is filtered off. The filtrate is concentrated under reduced pressure, and the residue is recrystallized from ethyl acetateisopropyl ether to give diethyl 2-[[N-(chloroacetyl)glycyl]amino]malonate (5.1 g), m.p. 104.5°-105° C.

後処理

  1. temperaturethe mixture is cooled to 0° to 5° C
  2. waitto stand at room temperature overnight
  3. filtrationInsoluble substance is filtered off from the reaction mixture
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. additionTo the residue is added ethyl acetate
  6. filtrationthe insoluble substance is filtered off
  7. concentrationThe filtrate is concentrated under reduced pressure
  8. customthe residue is recrystallized from ethyl acetateisopropyl ether

出典と根拠

ORDレコード
ord-1aa171324c1d4d6abdbf3e1423e3505a
出典データセット
uspto-grants-1989_12
特許番号
US04886894

反応ノート

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