Methanol → Boc-L-glutamine methyl ester

HRID 278852Notes

Reaction equation

HRID 278852 reaction equation
[NH:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].CO.[N+](=[CH2:22])=[N-]>CCOCC>[NH:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@H:2]([C:8]([O:10][CH3:22])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 9550DiazomethaneHCID 83687L-Glutamine, N2-((1,1-dimethylethoxy)carbonyl)-

Product 1

HCID 10956293Boc-L-glutamine methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of BOC-L-Gln (20 g, 81 mmol) in 50 mL of EtOAC and MeOH at 0° C. was added diazomethane in 250 mL of Et2O with stirring. The resulting yellow solution was stirred at 0° C. for 5 minutes and then warmed up to room temperature and stirred for 20 minutes. Argon gas was then bubbled through the yellow reaction mixture to remove excess diazomethane. The crude product was concentrated and purified by crystallization from methyl-tert-butyl ether. Yield 100%. 1H NMR (CDCl3) δ 1.45 (s, 9H), 1.96 (m, 1H), 2.21 (m, 1H), 2.36 (m, 2H), 3.76 (s, 3H), 4.34 (m, 1H), 5.32 (m, 1H), 5.44 (bs, 1H), 6.16 (bs, 1H). Anal. (C11H20N2O5) C, H, N.

Workup

  1. stirringThe resulting yellow solution was stirred at 0° C. for 5 minutes
  2. stirringstirred for 20 minutes
  3. customArgon gas was then bubbled through the yellow reaction mixture
  4. customto remove excess diazomethane
  5. concentrationThe crude product was concentrated
  6. custompurified by crystallization from methyl-tert-butyl ether

Sources & evidence

ORD record
ord-76bbcd9e44c044d49b78bd2cb56d75d6
Source dataset
uspto-grants-2002_03
Patent number
US06362166B1

Reaction notes

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