L-Glutamine, N2-((1,1-dimethylethoxy)carbonyl)- → tert-Butyl (2,6-dioxopiperidin-3-yl)carbamate

HRID 1009076Notes

Reaction equation

HRID 1009076 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:15]([OH:17])=O)[CH2:10][CH2:11][C:12](=[O:14])[NH2:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(C1NC=CN=1)(C1NC=CN=1)=O>C1COCC1>[O:17]=[C:15]1[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10][CH2:11][C:12](=[O:14])[NH:13]1

Participants

4

Reactant 2

HCID 83687L-Glutamine, N2-((1,1-dimethylethoxy)carbonyl)-HCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 11310728tert-Butyl (2,6-dioxopiperidin-3-yl)carbamateYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,6-Dioxo-3-(t-butoxycarbonylamino)piperidine (3) was prepared and isolated as follows. A solution of N-(t-butoxycarbonyl)-L-glutamine (4.92 g) and carbonyl diimidazole (1.70 g) in THF (100 mL) was refluxed for 9 h. The solvent was removed and the crude product was recrystallized from hot EtOAc to give compound 3 (2.04 g, 45%) as white crystals: mp 214-215° C.; 1H NMR (DMSO-d6) δ 4.22 (dd, J=6.2 Hz, J=11.0 Hz, 1H), 2.77-2.65 (m, 1H), 2.45 (m, 1 H), 1.96-1.87 (m, 2H), 1.40 (s, 9H); MS (CI/CH4) 227 [M−1]+.

Workup

  1. custom2,6-Dioxo-3-(t-butoxycarbonylamino)piperidine (3) was prepared
  2. customisolated
  3. customThe solvent was removed
  4. customthe crude product was recrystallized from hot EtOAc

Sources & evidence

ORD record
ord-cf3880e8290648ec88d3120a16219b05
Source dataset
uspto-grants-2011_07
Patent number
US07973057B2

Reaction notes

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