Triethylamine → HCID 86737420, compound

HRID 1733669Notes

Reaction equation

HRID 1733669 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(O[N:24]=[C:25]([C:31]#[N:32])[C:26]([O:28][CH2:29][CH3:30])=[O:27])(=O)=O.C(N(CC)CC)C>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([O:15][N:24]=[C:25]([C:31]#[N:32])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 101987Benzyloxycarbonyl-L-prolineHCID 54531055Ethyl cyano{[(methanesulfonyl)oxy]imino}acetate

Product 1

HCID 86737420HCID 86737420, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

N-Benzyloxycarbonyl-L-proline (1.25 g) and ethyl 2-methanesulfonyloxyimino-2-cyanoacetate (1.1 g) are dissolved in ethyl acetate (10 ml). To the solution is added triethylamine (0.7 ml) and the mixture is stirred at room temperature for 1 hour. After allowing to stand overnight, to the reaction mixture is added ethyl acetate. The mixture is washed with water and dried over anhydrous magnesium sulfate. After drying, the solvent is distilled off to give ethyl 2-(N-benzyloxycarbonyl-L-prolyloxyimino)-2-cyanoacetate (1.9 g) as an oily substance.

Workup

  1. waitto stand overnight, to the reaction mixture
  2. washThe mixture is washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter drying
  5. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-99f7c1b5fe27463d90be8ece501639ed
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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