Imidazole → HCID 59518835, 화합물

HRID 1161780노트

반응식

HRID 1161780 반응식
[OH:1][CH:2]([CH2:15][OH:16])[CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19].N1C=CN=C1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C=O)C.CO.CCOC(C)=O>[Si:21]([O:1][CH:2]([CH2:15][OH:16])[CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22]

참가 물질

8

반응물 4

HCID 795ImidazoleHCID 6101p-Toluenesulfonic acidHCID 28928tert-Butyldimethylsilyl chlorideHCID 3362144N-(Benzyloxycarbonyl)-3-amino-1,2-propanediol

생성물 1

HCID 59518835HCID 59518835, 화합물

시약·촉매·용매 3

HCID 887Methanol용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of benzyl 2,3-dihydroxypropylcarbamate in DMF (0.1 M) was added TBDMSCl (2.2 eq.) and imidazole (2.5 eq.) at room temperature. After stirred for 20 h, the reaction mixture was worked up with EtOAc, which was washed with water and brine. The organic layer was separated, dried and concentrated to give the crude bis-silylated product, which was dissolved in methanol (0.16 M) followed by addition of p-toluenesulfonic acid (0.1 equiv.) at 0° C. The reaction mixture was stirred for 1.5 h at the same temperature. After quenched with saturated NaHCO3 aqueous solution, the reaction mixture was extracted with EtOAc, which was washed with water and brine. The organic layer was separated, dried, concentrated, and purified on silica gel with 0-100% EtOAc/Hexanes gradient elution to provide the pure benzyl 2-(tert-butyldimethylsilyloxy)-3-hydroxypropylcarbamate.

후처리

  1. washwas washed with water and brine
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated
  5. customto give the crude bis-silylated product, which
  6. stirringThe reaction mixture was stirred for 1.5 h at the same temperature
  7. customAfter quenched with saturated NaHCO3 aqueous solution
  8. extractionthe reaction mixture was extracted with EtOAc, which
  9. washwas washed with water and brine
  10. customThe organic layer was separated
  11. customdried
  12. concentrationconcentrated
  13. custompurified on silica gel with 0-100% EtOAc/Hexanes gradient elution

출처 및 근거

ORD 기록
ord-49c34ead2d654796aa40eca11fa8b9bb
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820646B2

반응 노트

불러오는 중…