Sodium Bicarbonate → HCID 16098104, compound

HRID 600724Notes

Reaction equation

HRID 600724 reaction equation
[CH3:1][CH2:2][O:3][C:4](/[C:6](/Cl)=[N:7]\[OH:8])=[O:5].[C:10]([N:17]1[CH2:21][CH2:20][CH:19]=[CH:18]1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH2:2]([O:3][C:4]([C:6]1[C@@H:19]2[CH2:18][N:17]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:21][C@@H:20]2[O:8][N:7]=1)=[O:5])[CH3:1]

Participants

5

Reactant 3

HCID 516892Sodium Bicarbonate2×HCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetate2×HCID 10844857tert-Butyl 2,3-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 16098104HCID 16098104, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The title compound was prepared using commercially available ethyl chloro oximidoacetate (5). N-Boc-pyrroline (1.0 g; 5.91 mmol), ethyl chloro oximidoacetate (2.55 g; 16.8 mmol) and sodium bicarbonate (1.77 g; 21.06 mmol) in ethyl acetate (15 mL) were stirred for 54 hours. An additional amount of chloro oxime (2.6 g; 17.28 mmol) and sodium bicarbonate (2.1 g; 25.00 mmol) was added and the reaction mixture stirred overnight. The addition of reagents was repeated again and the reaction mixture stirred for 36 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was washed with water, brine, dried (MgSO4), filtered and evaporated. Cycloadduct 6 was isolated as a clear oil after chromatography with 20% ethyl acetate/hexanes.

Workup

  1. additionThe addition of reagents
  2. stirringthe reaction mixture stirred for 36 hours
  3. washwashed with water
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-107ad8ac7317494ea5d2579262b38169
Source dataset
uspto-grants-2011_03
Patent number
US07902227B2

Reaction notes

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