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

HRID 477204

반응식

HRID 477204 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1aa171324c1d4d6abdbf3e1423e3505a
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04886894

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