Benzyl succinimido carbonate → Benzyl (2r)-3-(4-cyanophenoxy)-2-hydroxypropylcarbamate

HRID 411541노트

반응식

HRID 411541 반응식
[NH2:1][CH2:2][C@@H:3]([OH:14])[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[CH2:15]([O:22][C:23](ON1C(=O)CCC1=O)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)(Cl)Cl.C(Cl)Cl>[C:10]([C:9]1[CH:12]=[CH:13][C:6]([O:5][CH2:4][C@H:3]([OH:14])[CH2:2][NH:1][C:23](=[O:24])[O:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:7][CH:8]=1)#[N:11]

참가 물질

5

반응물 2

HCID 83172Benzyl succinimido carbonateHCID 300720964-{[(2R)-3-Amino-2-hydroxypropyl]oxy}benzonitrile

생성물 1

HCID 91135093Benzyl (2r)-3-(4-cyanophenoxy)-2-hydroxypropylcarbamate수율 100%

시약·촉매·용매 2

HCID 6212Chloroform용매2회HCID 6344Dichloromethane용매

실험 절차

A mixture of 4{[(2R)-3-amino-2-hydroxypropyl]oxy}benzonitrile (see step (ii) above; 3.4 g, 17.7 mmol), TEA (2.69 g, 26.6 mmol) and CHCl3 (20 mL) was cooled to 0° C. before N-(benzyloxycarbonyloxy)succinimide (4.86 g, 19.5 mol) in CHCl3 (15 mL) was added slowly. The mixture was allowed to reach rt, and was stirred at that temperature overnight. The solvent was evaporated to give a residue that was dissolved in DCM. This solution was washed with water and brine and then dried (Na2SO4). Evaporation of the solvent gave 5.79 g (100%) of the sub-title compound.

후처리

  1. additionwas added slowly
  2. customto reach rt
  3. customThe solvent was evaporated
  4. customto give a residue that
  5. washThis solution was washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent

출처 및 근거

ORD 기록
ord-9df57f2bfb3e467fbbe6b80865b95060
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559162B2

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