Sodium ethoxide → HCID 12991311, compound

HRID 1250323Notes

Reaction equation

HRID 1250323 reaction equation
[CH2:1]([O:3][C:4](=[O:38])[CH:5]([C:19]1[CH:24]=[CH:23][C:22]([O:25][C@H:26]2[CH2:30][CH2:29][N:28]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:27]2)=[CH:21][CH:20]=1)[CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11]([C:17]#[N:18])=[CH:12][CH:13]=2)[CH:8]=1)[CH3:2].[O-]CC.[Na+]>C(O)C>[CH2:1]([O:3][C:4](=[O:38])[C@H:5]([C:19]1[CH:24]=[CH:23][C:22]([O:25][C@H:26]2[CH2:30][CH2:29][N:28]([CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:27]2)=[CH:21][CH:20]=1)[CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11]([C:17]#[N:18])=[CH:12][CH:13]=2)[CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxide2×HCID 12991310HCID 12991310, compound

Product 1

HCID 12991311HCID 12991311, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[4-[[(3S)-1-Benzyl-3-pyrrolidinyl]oxy]phenyl]-3-(7-cyano-2-naphthyl)propionic acid ethyl ester (5 g, 9.9 mmol) was heated and dissolved in ethanol (50 ml), and the resultant solution was cooled to room temperature with stirring to settle crystals. Subsequently, sodium ethoxide (100 mg, 1.5 mmol) was added thereto, followed by stirring at the same temperature for one hour, then sodium ethoxide (100 mg, 1.5 mmol) was further added, followed by stirring for 15 hours. The crystals were collected through filtration to obtain 2.9 g of the title compound (584 yield). The crystals had a diastereomer purity of 84% under HPLC analysis conditions. The crystals were dissolved in acetic acid ethyl ester (66 ml), and washed three times with water (50 ml). The resultant organic layer was concentrated under reduced pressure, and the residue was recrystallized twice from ethanol (14.5 ml, 12 ml) to obtain 2.0 g of the title compound (40% yield). The diastereomer purity of the crystals was 93%.

Workup

  1. stirringby stirring at the same temperature for one hour
  2. stirringby stirring for 15 hours
  3. filtrationThe crystals were collected through filtration

Sources & evidence

ORD record
ord-bdd80f206aba4bbca801b8e6840b4854
Source dataset
uspto-grants-2002_01
Patent number
US06337405B1

Reaction notes

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