Carbon Dioxide → HCID 449162, compound

HRID 1375688Notes

Reaction equation

HRID 1375688 reaction equation
C([O:4][CH2:5][C:6]1[C:7]([C:32]([O:34]CC)=[O:33])=[N:8][O:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13](/[CH:17]=[CH:18]/[CH2:19][O:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[C:22]=2[C:28]([O:30][CH3:31])=[O:29])[CH:12]=1)(=O)C.C([O-])([O-])=O.[K+].[K+].Cl.C(=O)=O>CCO.C1COCC1>[OH:27][C:23]1[C:22]([C:28]([O:30][CH3:31])=[O:29])=[C:21]([CH:26]=[CH:25][CH:24]=1)[O:20][CH2:19]/[CH:18]=[CH:17]/[C:13]1[CH:12]=[C:11]([C:10]2[O:9][N:8]=[C:7]([C:32]([OH:34])=[O:33])[C:6]=2[CH2:5][OH:4])[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 69508328HCID 69508328, compound

Product 1

HCID 449162HCID 449162, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-((acetyloxy)methyl)-5-(3-{(1E)-3-(3-hydroxy-2-(methoxycarbonyl)phenoxy)prop-1-enyl}phenyl)isoxazole-3-carboxylate (190 mg, 0.38 mmol) in EtOH (1.5 mL) was added 1 mL THF and 3 mL aqueous K2CO3 (sat'd). After 1.5 hour at ambient temperature 4 M HCl was added until CO2 evolution ceased. A precipitate formed which was filtered and dissolved in DMSO for purification by reverse phase HPLC (0–70% acetonitrile in 0.1% aqueous TFA) to provide the titled compound (100 mg, 61%). 1H NMR (300 MHz, DMSO-d6) δ 9.98 (s, 1H), 7.94 (broad s, 1H), 7.77 (broad d, J=7.8 Hz, 1H), 7.69 (broad d, J=7.8 Hz, 1H), 7.58 (t, J=7.8 Hz, 1H), 7.19 (t, J=8.3 Hz, 1H), 6.81 (broad d, J=16 Hz, 1H), 6.60 (d, J=8.3 Hz, 1H), 6.57 (dt, J=16, 5.2 Hz, 1H), 6.51 (d, J=8.3 Hz, 1H), 4.75 (d, J=5.2 Hz, 2H), 4.65 (s, 2H), 3.78 (s, 3H). MS (ESI+) m/z 426 (M+H)+, 443 (M+NH4)+, 448 (M+Na)+: (ESI−) m/z 424 (M−H)−, 380 (M−CO2H)−.

Workup

  1. customA precipitate formed which
  2. filtrationwas filtered
  3. dissolutiondissolved in DMSO for purification by reverse phase HPLC (0–70% acetonitrile in 0.1% aqueous TFA)

Sources & evidence

ORD record
ord-43c0a3c61ecc47a6984909667c6e826f
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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