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

HRID 1189904노트

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HRID 1189904 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%

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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-f91bb8ab9ebd4f4fac39e12135ccda7d
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674099B2

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