L-Glutamine → Phenylacetylglutamine
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]=1Participants
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. In either synthetic pathway, D-glutamine or a racemic mixture of glutamine stereoisomers can be used in place of L-glutamine, or D-isoglutamine or a racemic mixture of isoglutamine stereoisomers can be used in place of L-isoglutamine, yielding the corresponding optical isomer of phenylacetylglutamine. Either optical isomer of phenylacetylisoglutamine, or a mixture thereof in any proportion, can be used in the present invention.
Sources & evidence
- ORD record
- ord-0871b44a7c844900a113bd3af1c182b7
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06987131B1
Reaction notes
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