Ethanol → HCID 13190107, compound

HRID 1164380Notes

Reaction equation

HRID 1164380 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([NH:15][C@@H:16]([C:22](=[O:24])[NH2:23])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:26]1C=CC2N=NN(OS(C3C=CC(Cl)=CC=3)(=O)=O)C=2[CH:45]=1.C(O)C.C(OCC)(=O)C>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([NH:15][C@@H:16]([C:22](=[O:24])[NH2:23])[CH2:17][CH2:18][C:19]([O:21][CH2:26][CH3:45])=[O:20])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 122228411-(p-Chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazoleHCID 13190105HCID 13190105, compound

Product 1

HCID 13190107HCID 13190107, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of t-butyloxycarbonyl-L-valyl-D-isoglutamine (1.73 g, 5 mmol) in DMF (5 ml) was added TEA (0.84 ml) and 6-chloro-1-p-chlorobenzenesulfonyloxybenzotriazole (2.06 g, 6 mmol) under cooling. After being stirred at room temperature for 4 hours, the mixture was cooled with ice again and ethanol (3 ml) and TEA (0.7 ml) were added. The mixture was stirred at room temperature for 24 hours. Ethyl acetate (100 ml) was added to the reaction mixture and the organic layer was then washed with a 5% aqueous sodium bicarbonate solution, 1 N hydrochloric acid and water successively. The mixture was then dried over anhydrous sodium sulfate and evaporated. The crystalline residue was recrystallized from ethyl acetate/petroleum ether to obtain ethyl t-butyloxycarbonyl-L-valyl-D-isoglutaminate (820 mg). m.p. 128°-129° C. [α]D23 +8.4° (C 0.5, DMF). Rf2 =0.72, Rf3 =0.28.

Workup

  1. temperatureunder cooling
  2. temperaturethe mixture was cooled with ice again
  3. stirringThe mixture was stirred at room temperature for 24 hours
  4. washthe organic layer was then washed with a 5% aqueous sodium bicarbonate solution, 1 N hydrochloric acid and water successively
  5. dry with materialThe mixture was then dried over anhydrous sodium sulfate
  6. customevaporated
  7. customThe crystalline residue was recrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-e2ef2148f4e2470ebe397d6ccc660f8f
Source dataset
uspto-grants-1983_01
Patent number
US04369178

Reaction notes

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