L-Glutamine, N2-[(phenylmethoxy)carbonyl]- → HCID 66825788, compound

HRID 1525628Notes

Reaction equation

HRID 1525628 reaction equation
Cl.[NH2:2][CH:3]1[CH2:9][CH2:8][C:7](=[O:10])[NH:6][C:4]1=[O:5].[CH2:11]([O:18][C:19](N[C@H](C(O)=O)CCC(=O)N)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[CH2:11]([O:18][C:19]([N:6]1[C:7](=[O:10])[CH2:8][CH2:9][CH:3]([NH2:2])[C:4]1=[O:5])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 75855L-Glutamine, N2-[(phenylmethoxy)carbonyl]-HCID 1345483-Aminopiperidine-2,6-dione hydrochloride

Product 1

HCID 66825788HCID 66825788, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

α-aminoglutarimide hydrochloride is commercially unavailable internally. It is synthesized from N-benzyloxycarbony-L-glutamine, which reacts with N,N′-carbonyldiimidazole in THF refluxing to yield N-benzyloxycarbony-aminoglutarimide. After that amino protection group is removed and α-aminoglutarimide hydrochloride is yielded by hydrogenation under certain pressure catalyzed with Pd/C.

Sources & evidence

ORD record
ord-b44916c04cd94dce8cab6c8cfa724e77
Source dataset
uspto-grants-2015_07
Patent number
US09085530B2

Reaction notes

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