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

HRID 350356노트

반응식

HRID 350356 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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 δ 3.63 (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).

후처리

  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

출처 및 근거

ORD 기록
ord-705fe90267564c5b9a11ac666aea10a1
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179819B2

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