Hydrogen chloride-ethyl acetate → HCID 67371742, compound

HRID 1677069Notes

Reaction equation

HRID 1677069 reaction equation
Cl.C(OCC)(=O)C.C(OC([N:15]1[C@@H:19]([C@@H:20]([OH:22])[CH3:21])[CH2:18][CH2:17][C@H:16]1[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)=O)(C)(C)C>>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C@H:16]2[NH:15][C@@H:19]([C@@H:20]([OH:22])[CH3:21])[CH2:18][CH2:17]2)=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67371711HCID 67371711, compound

Product 1

HCID 67371742HCID 67371742, compoundYield 100%

Procedure

A 4 N hydrochloric acid/ethyl acetate (6.8 mL) solution of (2S,5R)-2-(4-fluorophenyl)-5-((S)-1-hydroxyethyl)-pyrrolidine-1-carboxylic acid t-butyl ester (708 mg, high polarity compound) was stirred for 1 hour at room temperature. The solvent was removed under a vacuum, and 5 N sodium hydroxide was added, and extraction was conducted twice with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum, and the title compound (479 mg) was obtained. The physical property values are as follows.

Workup

  1. customThe solvent was removed under a vacuum, and 5 N sodium hydroxide
  2. additionwas added
  3. extractionextraction
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under a vacuum

Sources & evidence

ORD record
ord-d6293508a2a049a694a8caed7304e1c1
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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