Formaldehyde → HCID 54698241, compound

HRID 2214644Notes

Reaction equation

HRID 2214644 reaction equation
[CH3:1][NH2:2].[CH2:3]=O.C[O:6][C:7](=O)[C:8]([OH:29])=[CH:9][C:10](=[O:28])[N:11]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1>CC(O)=O>[F:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][N:11]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C:10]([C:9]2[CH2:1][N:2]([CH3:3])[C:7](=[O:6])[C:8]=2[OH:29])=[O:28])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6329MethylamineHCID 69655528HCID 69655528, compound

Product 1

HCID 54698241HCID 54698241, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To 2 mL of AcOH at 60° C. was added 1 mL 2M MeNH2 (THF) and 60 mg paraformaldehyde. After stirring for 5 min 3-[bis-(4-fluoro-benzyl)-carbamoyl]-2-hydroxy-acrylic acid methyl ester (723 mg, 2.0 mmol) was added and the resulting solution stirred at 60° C. for 2 h. The reaction mixture was then cooled to room temperature and transferred to a separatory funnel. The solution was extracted with EtOAc, the organic layer separated, washed with H2O, satd NaCl, then dried over Na2SO4. After filtration the solvent was removed to isolate 500 mg (67% yield) of 4-hydroxy-1-methyl-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid bis-(4-fluoro-benzyl)-amide as an orange solid. MS (M+H) calcd for C20H19F2N2O3: 373.1. found: 373.0. 1H NMR (500 MHz, DMSO) δ: 2.94 (s, 3), 4.01 (s, 2), 4.46 (br s, 2), 4.55 (br s, 2), 7.13–7.22 (overlapping m, 8).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. customtransferred to a separatory funnel
  4. extractionThe solution was extracted with EtOAc
  5. customthe organic layer separated
  6. washwashed with H2O
  7. dry with materialdried over Na2SO4
  8. filtrationAfter filtration the solvent
  9. customwas removed

Sources & evidence

ORD record
ord-ec48ac908c72438289ad13f30ee44ac7
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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