L-Glutamine → N2-[(3-benzylphenylamino)carbonyl]-L-glutamine

HRID 1496663Notes

Reaction equation

HRID 1496663 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].[CH2:11]([C:18]1[CH:19]=[C:20]([N:24]=[C:25]=[O:26])[CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([C:18]1[CH:19]=[C:20]([NH:24][C:25]([NH:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6])=[O:26])[CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 5961L-GlutamineHCID 41227751-Benzyl-3-isocyanatobenzene

Product 1

HCID 67514037N2-[(3-benzylphenylamino)carbonyl]-L-glutamineYield 73%

Procedure

Preparation from L-(+)-glutamine (0.487 g, 3.33 mmol) and 3-benzylphenyl isocyanate (0.719 g, 3.33 mmol) (final pH value after 24 h stirring: 5-6) gave N2-[(3-benzylphenylamino)carbonyl]-L-glutamine (0.862 g, 73%, white solid).

Sources & evidence

ORD record
ord-c0cee37d136744ac9d98e9f815a00009
Source dataset
uspto-grants-2015_12
Patent number
US09198845B2

Reaction notes

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