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

HRID 1009085Notes

Reaction equation

HRID 1009085 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-a05343fbee2143bfb416854ec70e59ef
Source dataset
uspto-grants-2011_07
Patent number
US07973057B2

Reaction notes

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