Lithium Hydroxide → (S)-2-ethoxy-3-(3'-{[methyl-(1-phenylmethanoyl)amino]methyl}biphenyl-4-yl)propionic acid

HRID 584911Notes

Reaction equation

HRID 584911 reaction equation
C([C@H]1COC(=O)N1C(=O)[C@@H:15]([O:40][CH2:41][CH3:42])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:30]([CH3:39])[C:31](=[O:38])[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:24]=2)=[CH:19][CH:18]=1)C1C=CC=CC=1.C1[CH2:48][O:47]CC1.[OH-:49].[Li+]>O>[CH2:41]([O:40][C@@H:15]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:30]([CH3:39])[C:31]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[O:38])[CH:24]=2)=[CH:21][CH:22]=1)[C:48]([OH:47])=[O:49])[CH3:42]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 69694199N-{4'-[(S)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-2-ethoxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylbenzamide

Product 1

HCID 10273463(S)-2-ethoxy-3-(3'-{[methyl-(1-phenylmethanoyl)amino]methyl}biphenyl-4-yl)propionic acidYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

600 mg (1 mmol) of N-{4′-[(S)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-2-ethoxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylbenzamide and 10 ml of THF are introduced into a round-bottomed flask. At 0° C., 4.2 ml (2 mmol) of an aqueous lithium hydroxide solution (0.5M) are added and the mixture is stirred for one hour. The reaction medium is poured into water, acidified to pH 1 and extracted with ethyl acetate, and the organic phase is separated out after settling of the phases has taken place, dried over magnesium sulfate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (50/50). 200 mg (47%) of (S)-2-ethoxy-3-(3′-{[methyl-(1-phenylmethanoyl)amino]methyl}biphenyl-4-yl)propionic acid, with a melting point of 53-54° C., are obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase is separated out
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with a mixture of heptane and ethyl acetate (50/50)

Sources & evidence

ORD record
ord-5d4a5717dac2420fa4c5ecc8d083c066
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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