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Acetonitrile → (S)-1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine

HRID 343507
Notes
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Reaction equation

HRID 343507 reaction equation
C([C@](C(O)=O)(O)[C@](C(=O)C1C=CC(OC)=CC=1)(O)C(O)=O)(=O)C1C=CC(OC)=CC=1.[Cl:31][C:32]1[CH:33]=[C:34]([C@@:39]2([CH2:44][CH2:45][OH:46])[CH2:43][CH2:42][NH:41][CH2:40]2)[CH:35]=[CH:36][C:37]=1[Cl:38].C(#N)C.C(=O)(O)[O-].[Na+].[CH3:55][O:56][C:57]1[CH:65]=[CH:64][C:63]([N:66]2[CH:70]=[N:69][N:68]=[N:67]2)=[CH:62][C:58]=1[C:59](Cl)=[O:60]>O>[CH3:55][O:56][C:57]1[CH:65]=[CH:64][C:63]([N:66]2[CH:70]=[N:69][N:68]=[N:67]2)=[CH:62][C:58]=1[C:59]([N:41]1[CH2:42][CH2:43][C@@:39]([C:34]2[CH:35]=[CH:36][C:37]([Cl:38])=[C:32]([Cl:31])[CH:33]=2)([CH2:44][CH2:45][OH:46])[CH2:40]1)=[O:60]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 153920222-Methoxy-5-(1H-tetrazol-1-yl)benzoyl ChlorideHCID 131720896(S)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid

Product 1

HCID 53771624(S)-1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Combine (S)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt (0.14 g, 0.21 mmol) ethyl acetate (15 mL), acetonitrile (6 mL), water (6 mL), and sodium bicarbonate (0.09 g, 1.03 mmol). Cool to 0° C. in an salt-ice bath. Add 2-methoxy-5-(1H-tetrazol-1-yl)benzoyl chloride (0.21 mmol). After 30 minutes, warm to ambient temperature. After 30 minutes at ambient temperature, partition the reaction mixture between ethyl acetate and brine. Extract the organic layer with 1M hydrochloric acid solution, then saturated aqueous sodium bicarbonate solution. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. temperaturewarm to ambient temperature
  2. waitAfter 30 minutes at ambient temperature
  3. custompartition the reaction mixture between ethyl acetate and brine
  4. extractionExtract the organic layer with 1M hydrochloric acid solution
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfilter
  7. customevaporate in vacuo

Sources & evidence

ORD record
ord-8549219fe01b4cba9114d4c13796bd58
Source dataset
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05861417

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes