Citric Acid → ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(5-cyano-2-benzofuranyl)acrylate

HRID 361893

Reaction equation

HRID 361893 reaction equation
C(O[N:6]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18](=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:14][CH:13]=2)[C:7]1=C=O)(C)(C)C.[Cl-].[C:28]([C:30]1[CH:31]=[CH:32][C:33]2[O:37][C:36]([CH2:38][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:35][C:34]=2[CH:58]=1)#[N:29].[H-].[Na+].C(O)(=O)[CH2:62][C:63]([CH2:68]C(O)=O)([C:65](O)=O)[OH:64].[O:74]1CCC[CH2:75]1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C(O)C>[C:63]([O:64][C:75]([N:6]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[CH:14][C:15]([C:18](=[CH:38][C:36]3[O:37][C:33]4[CH:32]=[CH:31][C:30]([C:28]#[N:29])=[CH:58][C:34]=4[CH:35]=3)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][CH:17]=2)[CH2:7]1)=[O:74])([CH3:62])([CH3:65])[CH3:68]

Participants

8

Reactant 5

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 21844326(5-Cyano-2-benzofuranyl)methyltriphenylphosphonium chlorideHCID 86753663HCID 86753663, compound

Product 1

HCID 57233554ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(5-cyano-2-benzofuranyl)acrylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21584019Toluene ethylacetateSolvent

Procedure

3.12 g of ethyl 2 -[4 -[((3S)-1-tert-butoxy-carbonyl-3-pyrrolidinyl)oxy]phenyl]-2-oxoacetate was dissolved in 100 ml of tetrahydrofuran, followed by the addition of 4.65 g of (5-cyano-2-benzofuranyl)methyltriphenylphosphonium chloride. To the thus prepared solution was added 400 mg of 60% sodium hydride. With stirring, to the resulting mixture was added dropwise 3 ml of ethanol, followed by stirring at room temperature for 1 hour. The resulting reaction solution was neutralized with 10% citric acid solution, extracted with ethyl acetate, and then dried to distill off the solvent. Thereafter, the residue thus obtained was subjected to silica gel column chromatography using a toluene/ethyl acetate mixture as an elution solvent, thereby obtaining 3.1 g of ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(5-cyano-2-benzofuranyl)acrylate in the form of viscous oil as a mixture of E and Z forms. A portion of the thus obtained compound was separated into E and Z forms.

Workup

  1. stirringby stirring at room temperature for 1 hour
  2. customThe resulting reaction solution
  3. extractionextracted with ethyl acetate
  4. customdried
  5. distillationto distill off the solvent
  6. customThereafter, the residue thus obtained

Sources & evidence

ORD record
ord-795c793325ef45c486a007f251b35cdd
Source dataset
uspto-grants-1999_02
Patent number
US05866577

Linked notes

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