Ethylene carbonate → HCID 86583547, compound

HRID 1016779Notes

Reaction equation

HRID 1016779 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH2:23][CH3:24])[CH:17]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1)#[N:2].C1(=O)O[CH2:28][CH2:27][O:26]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:28][CH2:27][OH:26])=[C:18]([CH2:23][CH3:24])[CH:17]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 7303Ethylene carbonateHCID 86583548HCID 86583548, compound

Product 1

HCID 86583547HCID 86583547, compoundYield 24.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
155 °C

Procedure

A solution of the ethyl (RS)-(4-cyano-phenylamino)-(3-ethyl-4-hydroxy-phenyl)-acetate (400 mg, 1.23 mmol) described in Example 180.1, ethylene carbonate (110 mg, 1.23 mmol) and tetrabutylammonium bromide (264 mg, 1.23 mmol) in DMF (0.6 ml) was heated to 155° C. for 6 h. The reaction mixture was concentrated and the residue was purified by chromatography (SiO2, hexane/EtOAc 9:1). Ethyl (RS)-(4-cyano-phenylamino)-[3-ethyl-4-(2-hydroxy-ethoxy)-phenyl]-acetate (111 mg, 24%) was obtained as a yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chromatography (SiO2, hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-8d1fa0c1647846728f459ee1cf335978
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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