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

HRID 854276ノート

反応式

HRID 854276 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-89286bb8b89e49aeb96b844fc08de52d
出典データセット
uspto-grants-2007_08
特許番号
US07259160B2

反応ノート

読み込み中…