Hydrochloric Acid → HCID 68910452, compound

HRID 732689Notes

Reaction equation

HRID 732689 reaction equation
[C:1]1([C@H:11]([NH:13][CH2:14][C@@H:15]2[C@@H:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][N:17]([C:26]([C:28]3[CH:40]=[CH:39][C:31]([O:32][CH2:33][C:34]([O:36]CC)=[O:35])=[CH:30][CH:29]=3)=[O:27])[CH2:16]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Li+].[ClH:43]>C1COCC1.O>[ClH:43].[C:1]1([C@H:11]([NH:13][CH2:14][C@@H:15]2[C@@H:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][N:17]([C:26]([C:28]3[CH:29]=[CH:30][C:31]([O:32][CH2:33][C:34]([OH:36])=[O:35])=[CH:39][CH:40]=3)=[O:27])[CH2:16]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86628553HCID 86628553, compound

Product 1

HCID 68910452HCID 68910452, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of 174 mg of ethyl (4-{[(3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}phenoxy)acetate and 3.0 ml of a THF-water (2:1) mixed solvent was mixed with 22 mg of lithium hydroxide and stirred at room temperature. After completion of the reaction, this was neutralized by adding 1 M hydrochloric acid. This was extracted with chloroform, dried with anhydrous sodium sulfate and then concentrated under a reduced pressure. The thus obtained residue was purified by a fractional high performance liquid chromatography (acetonitrile-water) and then treated with hydrochloric acid to obtain 31 mg of (4-{[(3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}phenoxy)acetic acid hydrochloride as a colorless solid.

Workup

  1. additionmixed solvent
  2. customAfter completion of the reaction
  3. extractionThis was extracted with chloroform
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customThe thus obtained residue was purified by a fractional high performance liquid chromatography (acetonitrile-water)
  7. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-e4292d44ae11400f89d3955c03c14bd4
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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