Triethylamine → benzyl 4-[N'-(2-fluorophenyl)ureido]-3-methoxyphenylacetate

HRID 354296ノート

反応式

HRID 354296 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:4][C:3]=1[O:19][CH3:20].[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]=[C:29]=[O:30].CCN(CC)CC>C1COCC1>[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][C:29](=[O:30])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])=[CH:4][C:3]=1[O:19][CH3:20]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 855882-Fluorophenyl isocyanateHCID 23512273Benzyl 4-amino-3-methoxyphenylacetate

生成物 1

HCID 23512303benzyl 4-[N'-(2-fluorophenyl)ureido]-3-methoxyphenylacetate収率 100.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of benzyl 4-amino-3-methoxyphenylacetate (1.36 g, 5 mmol) in THF (20 mL) was added 2-fluorophenyl isocyanate (561 ul, 5 mmol) and a catalytic amount of Et3N. The resulting mixture was stirred for 3 hr. The mixture was quenched by the addition of H2O (10 mL) and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, and evaporated. The residue was chromatographed on silica-gel with CHCl3 as eluent to give 2.06 g (q.y.) benzyl 4-[N′-(2-fluorophenyl)ureido]-3-methoxyphenylacetate as a green oil. 1H-NMR (CDCl)3 δ3.63 (2H, s), 3.82 (3H, s), 5.14 (2H, s), 6.79-7.37 (12H, m), 8.01 (1H, d, J=7.8 Hz), 8.09-8.14 (1H, m).

後処理

  1. customThe mixture was quenched by the addition of H2O (10 mL)
  2. extractionextracted with EtOAc
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was chromatographed on silica-gel with CHCl3 as eluent

出典と根拠

ORDレコード
ord-f8e0afc6f0b1499d91852e2fb90f8cab
出典データセット
uspto-grants-2004_06
特許番号
US06756378B2

反応ノート

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