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

HRID 1291775Notes

Reaction equation

HRID 1291775 reaction equation
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]

Participants

6

Reactant 4

HCID 6287L-ValineHCID 6371Phosgene2×HCID 8134Diethylene Glycol Monomethyl EtherHCID 128583902-(2-Methoxyethoxy)ethyl carbonochloridate

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-3cb61179d4664840a30caece75fb21f2
Source dataset
uspto-grants-1998_05
Patent number
US05753652

Reaction notes

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