Monochloramine → HCID 90010382, compound

HRID 706794Notes

Reaction equation

HRID 706794 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([F:11])[CH:10]=1)=[O:5])[CH3:2].CC([O-])(C)C.[K+].Cl[NH2:19]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([NH2:19])[CH:8]=[C:9]([F:11])[CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 25423MonochloramineHCID 23665647Potassium tert-butoxideHCID 72212396HCID 72212396, compound

Product 1

HCID 90010382HCID 90010382, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-fluoro-1H-pyrrole-2-carboxylic acid ethyl ester (1.57 g, 10.0 mmol) in 20 ml DMF is added potassium tert-butylate (2.24 g, 20.0 mmol) under nitrogen. After stirring at room temperature for 90 minutes, the chloroamine solution from above (110 ml, ca. 25 mmol) is added slowly, after which the mixture is stirred for 5 minutes at room temperature. The reaction mixture is partitioned between saturated sodium bisulfite solution and tert-butyl methyl ether. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with cyclohexane/dichloromethane as eluent to afford 1-amino-4-fluoro-1H-pyrrole-2-carboxylic acid ethyl ester as white solid; HPLC/MS 2.21 min (B), [M+H] 173;

Workup

  1. stirringafter which the mixture is stirred for 5 minutes at room temperature
  2. customThe reaction mixture is partitioned between saturated sodium bisulfite solution and tert-butyl methyl ether
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated
  5. customThe residue is chromatographed on a silica gel column with cyclohexane/dichloromethane as eluent

Sources & evidence

ORD record
ord-f99a1c6d5c4c47dc8ce183096864b93b
Source dataset
uspto-grants-2015_11
Patent number
US09174995B2

Reaction notes

Loading…