4-Methylmorpholine → (S)-3-Methyl-2-[[methyl-(2-pyridinylmethyl)amino]carbonyl]aminobutyric acid methyl ester

HRID 53918

反応式

HRID 53918 の反応式
Cl.Cl.[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:9][O:10][C:11](=[O:20])[C@:12]([N:17]=[C:18]=[O:19])([CH:14]([CH3:16])[CH3:15])N.[CH3:21][N:22]1CCOC[CH2:23]1>ClCCl>[CH3:9][O:10][C:11](=[O:20])[C@H:12]([CH:14]([CH3:16])[CH3:15])[NH:17][C:18]([N:22]([CH3:23])[CH2:21][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=1)=[O:19]

参加物

5

反応物 3

HCID 79724-MethylmorpholineHCID 21954272Pyridine dihydrochlorideHCID 22845662a-Isocyanato-valine methyl ester

生成物 1

HCID 10039258(S)-3-Methyl-2-[[methyl-(2-pyridinylmethyl)amino]carbonyl]aminobutyric acid methyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 1.61 g (7.2 mmol) of 2-(N-methylamino)methyl)pyridine dihydrochloride and 1.14 g (7.2 mmol) of α-isocyanato-valine methyl ester in 40 ml of dichloromethane was treated with 2 ml (18 mmol) of 4-methylmorpholine. After being stirred for 2 h, the solution was partitioned between dichloromethane and water, dried over Na2SO4, and concentrated. Chromatography on silica gel using 2% methanol in chloroform provided 1.94 g (96%) of the desired compound (Rf 0.32, 5% methanol in chloroform) as a colorless oil. 1H NMR (CDCl3) δ 0.93 (d, J=7 Hz, 3 H), 0.97 (d, J=7 Hz, 3 H), 2.16 (m, 1 H), 3.03 (s, 3 H), 3.72 (s, 3 H), 4.43 (dd, J=8, 5 Hz, 1 H), 4.55 (s, 2 H), 6.15 (br, 1 H), 7.22 (dd, J=8, 6 Hz, 1 H), 7.28 (d, J=6 Hz, 1 H), 7.69 (br t, 1 H), 8.55 (d, J=5 Hz, 1 H).

後処理

  1. customthe solution was partitioned between dichloromethane and water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-80a7cafd71fb443197561932d17d9b14
出典データセット
uspto-grants-1997_04
特許番号
US05621109

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