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Water → 1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine

HRID 343522
Notes
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Reaction equation

HRID 343522 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.[C:31]1([C:37]2([CH2:42][CH2:43][OH:44])[CH2:41][CH2:40][NH:39][CH2:38]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.O.C(=O)([O-])[O-].[K+].[K+].[CH3:52][O:53][C:54]1[CH:62]=[CH:61][C:60]([N:63]2[CH:67]=[N:66][N:65]=[N:64]2)=[CH:59][C:55]=1[C:56](Cl)=[O:57]>CC(C)=O>[CH3:52][O:53][C:54]1[CH:62]=[CH:61][C:60]([N:63]2[CH:67]=[N:66][N:65]=[N:64]2)=[CH:59][C:55]=1[C:56]([N:39]1[CH2:40][CH2:41][C:37]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)([CH2:42][CH2:43][OH:44])[CH2:38]1)=[O:57]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 153920222-Methoxy-5-(1H-tetrazol-1-yl)benzoyl ChlorideHCID 70109704(-)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid

Product 1

HCID 184644561-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine

Reagents, catalysts & solvents

1
HCID 180AcetoneSolvent2×

Conditions

Temperature
0 °C

Procedure

Combine (-)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt (3.49 g,6.48 mmol) and acetone (20 mL), water (6 mL), and potassium carbonate (2.70 g, 19.5 mmol). Cool to 0° C. in an ice bath. After 30 minutes, add dropwise a solution of 2-methoxy-5-(1H-tetrazol-1-yl)benzoyl chloride (7.4 mmol) in acetone (20 mL). Warm to ambient temperature. After 18 hours, partition the reaction mixture between ethyl acetate and saturated aqueous sodium bicarbonate solution. Separate the organic layer and extract with brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. temperatureWarm to ambient temperature
  2. waitAfter 18 hours
  3. custompartition the reaction mixture between ethyl acetate and saturated aqueous sodium bicarbonate solution
  4. customSeparate the organic layer
  5. extractionextract with brine
  6. dry with materialDry the organic layer over Na2SO4
  7. filtrationfilter
  8. customevaporate in vacuo

Sources & evidence

ORD record
ord-e3b156bab3f94e8ea010d6fa3a63aa12
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