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

HRID 533361Notes

Reaction equation

HRID 533361 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-butoxy carbonyl)-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-07b87aa28cf64a38bd65173fe47fa36a
Source dataset
uspto-grants-2014_10
Patent number
US08853253B2

Reaction notes

Loading…