1,2-Dichloroethane → Tert-butyl {3-[methoxy(methyl)amino]-2-methyl-3-oxopropyl}carbamate

HRID 854276노트

반응식

HRID 854276 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([CH3:14])[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(N(CC)CC)C.Cl.[CH3:37][NH:38][O:39][CH3:40]>C(#N)C>[CH3:40][O:39][N:38]([CH3:37])[C:11](=[O:13])[CH:10]([CH3:14])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 41926403-((tert-Butoxycarbonyl)amino)-2-methylpropanoic acid

생성물 1

HCID 86607767Tert-butyl {3-[methoxy(methyl)amino]-2-methyl-3-oxopropyl}carbamate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

3-[(tert-Butoxycarbonyl)amino]-2-methylpropanoic acid (2.0 g, 9.9 mmol) was dissolved in acetonitrile (50 mL). To this solution was added HOBT (1.6 g, 11.85 mmol) and EDC (2.0 g, 10.4 mmol). The reaction was stirred at room temperature for 2 hr, and then treated with triethylamine (2.8 mL, 20 mmol) and N,O-dimethylhydroxyamine hydrochloride (2.0 g, 20 mmol). The reaction mixture was stirred at room temperature overnight. The reaction was quenched with water and extracted with ethyl acetate (3×). The combined organic extract was washed sequentially with 0.5N hydrochloric acid, 1N aqueous sodium bicarbonate solution and brine, dried over sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on a Biotage® system (silica, 40-100% ethyl acetate in hexanes) to yield tert-butyl {3-[methoxy(methyl)amino]-2-methyl-3-oxopropyl}carbamate as white solid. MS (M+1−Boc): 147.

후처리

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate (3×)
  4. extractionThe combined organic extract
  5. washwas washed sequentially with 0.5N hydrochloric acid, 1N aqueous sodium bicarbonate solution and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by flash chromatography on a Biotage® system (silica, 40-100% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-89286bb8b89e49aeb96b844fc08de52d
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259160B2

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