3-Bromo-1,1-diethoxypropan-2-one → 2-Amino-4-diethoxymethyl-imidazole-1-carboxylic acid tert-butyl ester

HRID 43219노트

반응식

HRID 43219 반응식
Br[CH2:2][C:3](=O)[CH:4]([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7].[C:12]([O:16][C:17]([NH:19][C:20]([NH2:22])=[NH:21])=[O:18])([CH3:15])([CH3:14])[CH3:13]>>[C:12]([O:16][C:17]([N:19]1[CH:2]=[C:3]([CH:4]([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])[N:21]=[C:20]1[NH2:22])=[O:18])([CH3:15])([CH3:13])[CH3:14]

참가 물질

3

반응물 2

HCID 592929443-Bromo-1,1-diethoxypropan-2-oneHCID 178454308HCID 178454308, 화합물

생성물 1

HCID 592928212-Amino-4-diethoxymethyl-imidazole-1-carboxylic acid tert-butyl ester수율 41.7%

반응 조건

온도
50 °C

실험 절차

A mixture of 3-bromo-1,1-diethoxy-propan-2-one (21.3 g, 95 mmol) (Step 179.9) and N-tert-butoxycarbonylguanidine (45.3 g, 284 mmol, 3 equiv) (Step 179.10) was stirred at 50° C. for 8 h. The reaction mixture was concentrated, diluted in EtOAc/H2O and extracted with EtOAc. The organic phase was washed with water and brine, dried (Na2SO4) and concentrated. The residue was purified by silica gel column chromatography (DCM/EtOAc, 3:7) followed by trituration in Et2O to afford 11.3 g of the title compound as a white solid: ES-MS: 286 [M+H]+; Rf=0.34 (DCM/EtOAc, 3:7).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted in EtOAc/H2O
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (DCM/EtOAc, 3:7)

출처 및 근거

ORD 기록
ord-dd95928b5762494a87f756c33c6c7ac9
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536175B2

반응 노트

불러오는 중…