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

HRID 2220818노트

반응식

HRID 2220818 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-96098b95748e45f6bc979c27a525dc70
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07368424B2

반응 노트

불러오는 중…