p-Toluenesulfonic acid monohydrate → 4-(2-Oxoethyl)benzyl 3-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl) phenoxy)methyl)benzoate

HRID 877320Notes

Reaction equation

HRID 877320 reaction equation
[C:1]1([C@H:7]([NH:38][C:39]([O:41][C@@H:42]2[CH:47]3[CH2:48][CH2:49][N:44]([CH2:45][CH2:46]3)[CH2:43]2)=[O:40])[C:8]2[CH:9]=[C:10]([CH:35]=[CH:36][CH:37]=2)[O:11][CH2:12][C:13]2[CH:14]=[C:15]([CH:32]=[CH:33][CH:34]=2)[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH:27](OC)[O:28]C)=[CH:22][CH:21]=2)=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.C(=O)([O-])O.[Na+]>[C:1]1([C@H:7]([NH:38][C:39]([O:41][C@@H:42]2[CH:47]3[CH2:48][CH2:49][N:44]([CH2:45][CH2:46]3)[CH2:43]2)=[O:40])[C:8]2[CH:9]=[C:10]([CH:35]=[CH:36][CH:37]=2)[O:11][CH2:12][C:13]2[CH:14]=[C:15]([CH:32]=[CH:33][CH:34]=2)[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH:27]=[O:28])=[CH:22][CH:21]=2)=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 867208184-(2,2-dimethoxyethyl)benzyl 3-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)phenoxy)methyl)benzoate

Product 1

HCID 867208214-(2-Oxoethyl)benzyl 3-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl) phenoxy)methyl)benzoate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of 4-(2,2-dimethoxyethyl)benzyl 3-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)phenoxy)methyl)benzoate (0.100 g, 0.15 mmol) in acetone (5 mL) was added para-toluenesulfonic acid monohydrate (0.086 g, 0.45 mmol) and the mixture stirred at RT for 1 hour. The reaction mixture was diluted with saturated sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure. The residue was used in the next step with no further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  3. filtrationfiltered
  4. customthe solvent evaporated at reduced pressure
  5. customThe residue was used in the next step with no further purification

Sources & evidence

ORD record
ord-0aa4206b3ed54ecba0d179a058a1686a
Source dataset
uspto-grants-2015_03
Patent number
US08987299B2

Reaction notes

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