Dimethylformamide → 1-(N-benzyloxycarbonyl-L-valyloxy)-2-methyl-2-propanol

HRID 489031

반응식

HRID 489031 반응식
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:34][C:35]([OH:39])([CH3:38])[CH2:36]O.CN(C=O)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH2:34][C:35]([CH3:38])([OH:39])[CH3:36])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 684102-Methylpropane-1,2-diolHCID 726987N-Carbobenzoxy-L-valine

생성물 1

HCID 540342421-(N-benzyloxycarbonyl-L-valyloxy)-2-methyl-2-propanol수율 88.9%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

반응 조건

온도
10 °C

실험 절차

N-Benzyloxycarbonyl-L-valine (2.02 g, 8.0 mmol), 4-dimethylaminopyridine (100 mg, 0.8 mmol), and), and dicyclohexylcarbodiimide (2.04 g, 9.9 mmol, is 20 mL CH2Cl2) were added to 2-methyl-1,2-propanediol (12.2 mmol) in 30 mL dry CH2Cl2, with cooling in an ice bath. DMF (5 mL) was added. After stirring for 5 h at 10° C., the reaction mixture was filtered, concentrated, and then redissolved in ethyl acetate. The organic solution was washed with saturated NaCl, dried over anhydrous Na2SO4, and concentrated. Flash column chromatography (silica, 2/1 petroleum ether-ethyl acetate) gave 2.3 g of the title compound.

후처리

  1. temperaturewith cooling in an ice bath
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated
  4. dissolutionredissolved in ethyl acetate
  5. washThe organic solution was washed with saturated NaCl
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-99783b6fb4d54fcf9e08d10e8ed010ff
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06974802B2

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