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

HRID 76979
Notes
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Reaction equation

HRID 76979 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6342
Acetonitrile
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-1356093da1324836bc8a0daf4a9f0b7c
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08835682B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes