Sodium Bicarbonate → HCID 131725404, compound

HRID 1349020Notes

Reaction equation

HRID 1349020 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[NH:4][C:5]([C@@H:7]1[CH2:11][C:10](=[N:12][O:13][CH3:14])[CH2:9][N:8]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=O.C(=O)(O)[O-].[Na+]>ClCCl.C(O)(=O)C>[NH:4]1[C:3]2[CH:22]=[CH:23][CH:24]=[CH:25][C:2]=2[N:1]=[C:5]1[C@@H:7]1[CH2:11][C:10](=[N:12][O:13][CH3:14])[CH2:9][N:8]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 131725403HCID 131725403, compound

Product 1

HCID 131725404HCID 131725404, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the anilide compound from the previous step, e.g. tert-butyl (2S,4EZ)-2-[(2-aminoanilino)carbonyl]-4-(methoxyimino)-1-pyrrolidinecarboxylate (0.8 g, 2.3 mmol) in dichloromethane (30 ml) and acetic acid (3 ml) was stirred at room temperature for 3 days. Saturated aqueous sodium bicarbonate (7 ml) was added to the reaction, the organic phase collected and dried over magnesium sulfate before filtering and removal of solvent in vacuo to give the desired product, e.g. tert-butyl (2S,4EZ)-2-(1H-benzimidazol-2-yl)-4-(methoxyimino)-1-pyrrolidinecarboxylate (740 mg, 97%) as an off-white foam.

Workup

  1. customthe organic phase collected
  2. dry with materialdried over magnesium sulfate
  3. filtrationbefore filtering
  4. customremoval of solvent in vacuo

Sources & evidence

ORD record
ord-50ed98707bf142aa8f912a9654939b5e
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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