Formaldehyde → HCID 54698241、化合物

HRID 2214644ノート

反応式

HRID 2214644 の反応式
[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

参加物

5

反応物 3

HCID 712FormaldehydeHCID 6329MethylamineHCID 69655528HCID 69655528、化合物

生成物 1

HCID 54698241HCID 54698241、化合物収率 67%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ec48ac908c72438289ad13f30ee44ac7
出典データセット
uspto-grants-2006_09
特許番号
US07109186B2

反応ノート

読み込み中…