Nitromethane → HCID 69688505, compound

HRID 1368076Notes

Reaction equation

HRID 1368076 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH:20]1[CH2:22][CH2:21]1)[CH:13]=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C(N(C)C)=N.[N+:31]([CH3:34])([O-:33])=[O:32]>>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH:20]1[CH2:22][CH2:21]1)[CH:13]([CH2:34][N+:31]([O-:33])=[O:32])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 664601,1,3,3-TetramethylguanidineHCID 69688152HCID 69688152, compound

Product 1

HCID 69688505HCID 69688505, compoundYield 96.1%

Procedure

Ethyl 4-(S)-benzyloxycarbonylamino-4-cyclopropyl-2-butenoate was dissolved in dry nitromethane (15 ml), and the solution was mixed with 1,1,3,3-tetramethylguanidine (133 μl, 1.05 mol) and stirred at room temperature for 17 hours. The reaction solution was concentrated under a reduced pressure, the resulting residue was dissolved in chloroform (50 ml), and the solution was washed with 10% citric acid aqueous solution (50 ml) and saturated sodium chloride aqueous solution (50 ml) in that order, and then dried over anhydrous magnesium sulfate, thereby obtaining 1.207 g (96.1%) of the title compound as a yellow oil. This product (diastereomer mixture) was used in the subsequent reaction without purification.

Workup

  1. concentrationThe reaction solution was concentrated under a reduced pressure
  2. dissolutionthe resulting residue was dissolved in chloroform (50 ml)
  3. washthe solution was washed with 10% citric acid aqueous solution (50 ml) and saturated sodium chloride aqueous solution (50 ml) in that order
  4. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-48e1186bf58d4fae8ecc7b4d4f1d012d
Source dataset
uspto-grants-2003_06
Patent number
US06573260B1

Reaction notes

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