1-Hydroxybenzotriazole → 2-({[(R)-(1-aza-bicyclo[2.2.2]oct-3-yl)oxycarbonyl]-phenyl-methyl}-amino)-benzoic acid methyl ester

HRID 76979

반응식

HRID 76979 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][CH:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13]([OH:15])=[O:14])=[O:4].C(N(C(C)C)C(C)C)C.C1C=CC2N(O)N=NC=2C=1.[N:41]12[CH2:48][CH2:47][CH:44]([CH2:45][CH2:46]1)[C@@H:43](O)[CH2:42]2>C1COCC1.CC#N>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][CH:12]([C:13]([O:15][C@@H:43]1[CH:44]2[CH2:47][CH2:48][N:41]([CH2:46][CH2:45]2)[CH2:42]1)=[O:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

6

반응물 3

HCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 67425438N-ethyl-N-isopropylpropan-2-amine 2-(2-(methoxycarbonyl)phenylamino)-2-phenylacetate

생성물 1

HCID 468405712-({[(R)-(1-aza-bicyclo[2.2.2]oct-3-yl)oxycarbonyl]-phenyl-methyl}-amino)-benzoic acid methyl ester수율 16%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매

실험 절차

N-ethyl-N-isopropylpropan-2-amine 2-(2-(methoxycarbonyl)phenylamino)-2-phenylacetate (I34) (611 mg, 1.47 mmol), 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (559 mg, 1.47 mmol), and HOBT (226 mg, 1.47 mmol) are dissolved in THF (7 mL) and MeCN (3 mL). (R)-Quinuclidin-3-ol (375 mg, 2.95 mmol) is added and the mixture is stirred at RT for 1 hour. Solvents are evaporated, the residue is dissolved in EtOAc and washed with sat. NaHCO3, water and brine. The organic layer is recovered, dried over Na2SO4, filtered and evaporated. The crude is purified by preparative HPLC and the collected fractions are evaporated, the residue is dissolved in EtOAc and washed with NaHCO3 and brine. The organic layer is recovered, dried over Na2SO4, filtered and evaporated to afford compound the title compound as a colorless compound (95 mg, 16% yield, mixture of diastereoisomers).

후처리

  1. customSolvents are evaporated
  2. dissolutionthe residue is dissolved in EtOAc
  3. washwashed with sat. NaHCO3, water and brine
  4. customThe organic layer is recovered
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude is purified by preparative HPLC
  9. customthe collected fractions are evaporated
  10. dissolutionthe residue is dissolved in EtOAc
  11. washwashed with NaHCO3 and brine
  12. customThe organic layer is recovered
  13. dry with materialdried over Na2SO4
  14. filtrationfiltered
  15. customevaporated

출처 및 근거

ORD 기록
ord-1356093da1324836bc8a0daf4a9f0b7c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835682B2

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