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L-Valine → N-(2-(2-Methoxyethoxy)-ethoxy)carbonyl-(L)-valine

HRID 1291775
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HRID 1291775 반응식
COCCOCCO.C(Cl)(Cl)=O.[NH2:13][C@H:14]([C:18]([OH:20])=[O:19])[CH:15]([CH3:17])[CH3:16].[CH3:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][C:29](Cl)=[O:30]>C1(C)C=CC=CC=1>[CH3:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][C:29]([NH:13][C@H:14]([C:18]([OH:20])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:30]
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참가 물질

6

반응물 4

HCID 6287L-ValineHCID 6371Phosgene2회HCID 8134Diethylene Glycol Monomethyl EtherHCID 128583902-(2-Methoxyethoxy)ethyl carbonochloridate

생성물 1

HCID 54169760N-(2-(2-Methoxyethoxy)-ethoxy)carbonyl-(L)-valine

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

19.8 ml (168 mmol) of diethylene glycol monomethyl ether are added dropwise at 0° to 100 ml of a 20% solution of phosgene in toluene and the mixture is stirred overnight at RT. Excess phosgene is expelled with nitrogen and the reaction solution is washed with water and concentrated by evaporation. Analogously to Example 1c, 10 g (85.4 mmol) of (L)-valine are added to the crude 2-(2-methoxyethoxy)ethylchloroformate (15.6 g, 85.4 mmol) yielding the title compound in the form of a colourless resin. 1H-NMR (200 MHz, CD3OD): 4.18 (m, 2H), 4.05 d, J=6 Hz, 1H), 3.72-3.40 (m, 8H), 3.35 (s, 3H), 2.18 (m, 1H), 0.95 (t, J=7H, 6H).

후처리

  1. washthe reaction solution is washed with water
  2. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-3cb61179d4664840a30caece75fb21f2
출처 데이터셋
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05753652

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