Aerosporin → (Z)-2-Methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-acrylic Acid Methyl Ester

HRID 902453Notes

Reaction equation

HRID 902453 reaction equation
[CH3:1][O:2][C:3](=[O:33])[CH:4]([O:31][CH3:32])[CH:5](O)[C:6]1[C:11]2[S:12][CH:13]=[CH:14][C:10]=2[C:9]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:8][CH:7]=1.CCC(CCCCC(NC(C(NC(C(NC(C(NC1C(=O)NC(CCN)C(=O)NC(CC2C=CC=CC=2)C(=O)NC(CC(C)C)C(=O)NC(CCN)C(=O)NC(CCN)C(=O)NC(C(O)C)C(=O)NCC1)=O)CCN)=O)C(O)C)=O)CCN)=O)C.OS(O)(=O)=O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:33])/[C:4](/[O:31][CH3:32])=[CH:5]/[C:6]1[C:11]2[S:12][CH:13]=[CH:14][C:10]=2[C:9]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[O:21][C:22]=2[CH3:23])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 5702105AerosporinHCID 589954383-Hydroxy-2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic Acid Methyl Ester

Product 1

HCID 11259455(Z)-2-Methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-acrylic Acid Methyl EsterYield 90.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2.50 g of 3-hydroxy-2-methoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-yl}-propionic acid methyl ester (5.25 mmol, syn/anti mixture of 1:4) was dissolved at room temperature in 25 ml of DMF. After the addition of 0.59 ml of conc. sufuric acid (10.5 mmol), the brown solution was stirred at 100° C. for 15 h. During cooling the reaction solution to r.t., the product crystallized. Under stirring, 15 ml of methanol were added at r.t. and the suspension stirred for 1 h at 0° C. The white crystals were filtered off, washed with 25 ml of cold (−15° C.) methanol in two portions and dried to constant weight (20° C./5 mbar/16h) to afford 2.13 g (90%) of the title compound with a purity of 99.5% (GC area).

Workup

  1. temperatureDuring cooling the reaction solution to r.t.
  2. customthe product crystallized
  3. stirringUnder stirring
  4. addition15 ml of methanol were added at r.t.
  5. stirringthe suspension stirred for 1 h at 0° C
  6. filtrationThe white crystals were filtered off
  7. washwashed with 25 ml of cold (−15° C.) methanol in two portions
  8. dry with materialdried to constant weight (20° C./5 mbar/16h)

Sources & evidence

ORD record
ord-3daf17ba6533441e85c36cd56e94aa04
Source dataset
uspto-grants-2008_04
Patent number
US07365207B2

Reaction notes

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