L-Glutamine → HCID 86719907, compound

HRID 1496661Notes

Reaction equation

HRID 1496661 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].[OH-].[Na+].[CH2:13]([CH:15]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][N:17]=[C:18]=[O:19])[CH3:14]>O.O1CCOCC1>[CH2:13]([CH:15]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][NH:17][C:18]([NH:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6])=[O:19])[CH3:14]

Participants

5

Reactant 3

HCID 5961L-GlutamineHCID 14798Sodium HydroxideHCID 126142993-(Isocyanatomethyl)heptane

Product 1

HCID 86719907HCID 86719907, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

At 5° C., a suspension of L-(+)-glutamine (23.1 g, 158 mmol) in 1:1 water/dioxane (300 ml) was treated successively with a solution of 2N aq. NaOH (79 ml) and with 2-ethylhexyl isocyanate (25 g, 158 mmol). The resulting mixture was stirred for 24 h while its temperature rose to 20° C. (final pH value: 6) and filtered. The filtrate was washed twice with ethyl acetate (200 ml) and the combined organic phases were acidify with a 2N aq. HCl solution to pH 1. Filtration of the resulting precipitate and drying under vacuum gave N2-[(2-ethylhexylamino)carbonyl]-L-glutamine (42 g, 88%, white solid).

Workup

  1. customrose to 20° C.
  2. filtrationfiltered
  3. washThe filtrate was washed twice with ethyl acetate (200 ml)
  4. filtrationFiltration of the resulting precipitate
  5. customdrying under vacuum

Sources & evidence

ORD record
ord-bddc4e1bf68b4a66a509a3f02032a1ab
Source dataset
uspto-grants-2015_12
Patent number
US09198845B2

Reaction notes

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