Triethylamine → 4-[3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl]-2,5-difluoro-3-methoxybenzoic acid ethyl ester

HRID 10284노트

반응식

HRID 10284 반응식
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[C:9]([F:11])[C:8](F)=[C:7]([O:13][CH3:14])[C:6]=1[F:15])[CH3:2].[C:17]([O:21][C:22](=[O:29])[NH:23][CH:24]1[CH2:28][CH2:27][NH:26][CH2:25]1)([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C>C(#N)C>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[C:9]([F:11])[C:8]([N:26]2[CH2:27][CH2:28][CH:24]([NH:23][C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:29])[CH2:25]2)=[C:7]([O:13][CH3:14])[C:6]=1[F:15])[CH3:2]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 2774387Benzoic acid, 2,4,5-trifluoro-3-methoxy-, ethyl ester

생성물 1

HCID 210411814-[3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl]-2,5-difluoro-3-methoxybenzoic acid ethyl ester수율 77.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 2,4,5-trifluoro-3-methoxybenzoic acid ethyl ester (Example 1f, 2.821 g, 12.05 mmol), pyrrolidin-3-ylcarbamic acid tert-butyl ester (3.310 g, 17.77 mmol), and triethylamine (9.13 g, 12.6 mL, 90.23 mmol) in acetonitrile (50 mL) is heated at 40° C. under nitrogen for 2 days. The yellow solution is concentrated to near dryness and poured into saturated NaHCO3 solution and extracted with dichloromethane. The combined organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum. The resulting residue is purified by flash column chromatography (1:7 ethyl acetate/hexanes) to afford the title compound as a yellow solid (3.743 g). MS EI: m/z 401 (MH+).

후처리

  1. concentrationThe yellow solution is concentrated
  2. additionpoured into saturated NaHCO3 solution
  3. extractionextracted with dichloromethane
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe resulting residue is purified by flash column chromatography (1:7 ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-f2ce1d24c4af410d90ca4f96147cdb48
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094780B1

반응 노트

불러오는 중…