1,2-Dichloroethane → N-(tert-Butoxycarbonyl)-3-(tert-butyl)-D-alanyl-3-(3-pyridyl)-L-alanine methyl ester

HRID 2220818ノート

反応式

HRID 2220818 の反応式
CN1CCOCC1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:22]([O:26][C:27]([NH:29][C@@H:30]([C:36]([OH:38])=O)[CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:28])([CH3:25])([CH3:24])[CH3:23].[CH3:39][O:40][C:41](=[O:51])[C@H:42]([CH2:44][C:45]1[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=1)[NH2:43]>ClCCl>[CH3:39][O:40][C:41](=[O:51])[C@H:42]([CH2:44][C:45]1[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=1)[NH:43][C:36](=[O:38])[C@@H:30]([CH2:31][C:32]([CH3:33])([CH3:34])[CH3:35])[NH:29][C:27]([O:26][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:28]

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 5706551Methyl (S)-2-amino-3-(pyridin-3-yl)propanoateHCID 7021114(R)-2-((tert-Butoxycarbonyl)amino)-4,4-dimethylpentanoic acid

生成物 1

HCID 59709769N-(tert-Butoxycarbonyl)-3-(tert-butyl)-D-alanyl-3-(3-pyridyl)-L-alanine methyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

N-methylmorpholine (5 equivalents, 6.0 mmol), EDC (2.5 equivalents, 3.0 mmol) and HOBt (2.5 equivalents, 3.0 mmol) are added slowly to a solution of N-(tert-butoxycarbonyl)-3-tert-butyl-D-alanine (1.0 equivalent, 1.2 mmol) and 3-(3-pyridyl)-L-alanine methyl ester (1.0 equivalent, 1.2 mmol) in dry dichloromethane (3 ml) at −30° C. The reaction mixture slowly (approx. 12 h) warms to room temperature, with complete conversion being observed by means of HPLC (method 36). The reaction mixture is worked up by diluting with dichloromethane (20 ml) and washing with saturated sodium bicarbonate solution (10 ml). The organic phase is dried with magnesium sulphate, filtered and concentrated. The crude product is purified by flash chromatography (silica gel, gradient dichloromethane 100% to dichloromethane/methanol: 4/1), resulting in 466 mg (96% of theory) of product.

後処理

  1. customThe reaction mixture slowly (approx. 12 h)
  2. customwarms to room temperature, with complete conversion
  3. washwashing with saturated sodium bicarbonate solution (10 ml)
  4. dry with materialThe organic phase is dried with magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by flash chromatography (silica gel, gradient dichloromethane 100% to dichloromethane/methanol: 4/1)
  8. customresulting in 466 mg (96% of theory) of product

出典と根拠

ORDレコード
ord-96098b95748e45f6bc979c27a525dc70
出典データセット
uspto-grants-2008_05
特許番号
US07368424B2

反応ノート

読み込み中…