L-Glutamine → Phenylacetylglutamine

HRID 496090Notes

Reaction equation

C1(CC(N[C@H](C(=O)N)CCC(O)=O)=O)C=CC=CC=1.[C:20]1([CH2:26][C:27](Cl)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[NH2:30][C@H:31]([C:37]([OH:39])=[O:38])[CH2:32][CH2:33][C:34](=[O:36])[NH2:35]>>[C:20]1([CH2:26][C:27]([NH:30][C@H:31]([C:37]([OH:39])=[O:38])[CH2:32][CH2:33][C:34](=[O:36])[NH2:35])=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Reactant 3

HCID 5961L-Glutamine

HCID 7679Phenylacetyl chloride

HCID 9939588Phenylacetylisoglutamine

Product 1

HCID 92258Phenylacetylglutamine

Procedure

Phenylacetylisoglutamine can be synthesized by the reaction of phenylacetyl chloride with L-glutamine to yield phenylacetylglutamine, with subsequent heating under vacuum at 160° C. to yield 3-phenylacetylamino-2,6-piperidinedione, which can then be treated with sodium hydroxide. Also, phenylacetylisoglutamine can be prepared by treatment of phenylacetic acid with N,N′-disuccinimidyl carbonate in acetonitrile followed by reaction with L-isoglutamine in the presence of NaHCO3 in a 1:1 acetonitrile/water mixture. However, the second synthesis requires L-isoglutamine, which is expensive, so the former route of synthesis is preferred on economic grounds.

Sources & evidence

ORD record: ord-8cbaa5388ad4447cbdaabc835e25347f
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06943192B2

Reaction notes

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