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

HRID 1036664Notes

Reaction equation

HRID 1036664 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>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:10][CH2:11][C:12](=[O:14])[NH:13][C:15]1=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

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

A mixture of N-(tert-butoxycarbonyl)-L-glutamine (4.92 g, 20 mmol) and carbonyl diimidazole (3.24 g, 20 mmol) in THF (100 mL) was refluxed for 16 h. Thereafter, solvent was removed and the crude product was recrystallized from hot EtOAc to give compound 203 (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, 1H), 1.96-1.87 (m, 2H), 1.40 (s, 9H); MS (CI/CH4) m/z 227 [M−1]+.

Workup

  1. temperaturewas refluxed for 16 h
  2. customThereafter, solvent was removed
  3. customthe crude product was recrystallized from hot EtOAc

Sources & evidence

ORD record
ord-2a3682f0f01b42b1985f48c3d06f5b07
Source dataset
uspto-grants-2013_10
Patent number
US08546430B2

Reaction notes

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