Hydrochloric Acid → HCID 178435518, compound

HRID 2211395Notes

Reaction equation

HRID 2211395 reaction equation
C([O:3][C:4]([CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([C:37]2[NH:41][N:40]=[N:39][N:38]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]2[CH:26]=[C:25]([OH:27])[C:24]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)=[CH:23][C:22]=2[CH2:35][CH3:36])=[CH:10][CH:9]=1)=[O:5])C.C(=O)([O-])[O-].[Na+].[Na+].Cl>C(O)C>[C:4]([CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([C:37]2[NH:41][N:40]=[N:39][N:38]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]2[CH:26]=[C:25]([OH:27])[C:24]([C:28]3[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=3)=[CH:23][C:22]=2[CH2:35][CH3:36])=[CH:10][CH:9]=1)([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 178472969HCID 178472969, compound

Product 1

HCID 178435518HCID 178435518, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Crude 1-(4-(ethoxycarbonylmethoxy)phenyl)-1-(1H-tetrazol-5-yl)-6-(2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy)hexane (50 mg) was dissolved in ethanol (20 mL). 1M Aqueous sodium carbonate solution was added and the resultant solution stirred at room temperature for 3 hours. The pH of the solution was then adjusted to 2 using 1M hydrochloric acid and the solution extracted 5 times with chloroform. The combined chloroform extracts were dried with magnesium sulfate and evaporated to an oil which was purified on a reverse phase HPLC C18 column eluting with methanol/water (85:15) and 0.1% acetic acid. On removal of the solvent 9.7 mg of the title compound was obtained as a colorless oil. MS, NMR.

Workup

  1. extractionthe solution extracted 5 times with chloroform
  2. dry with materialThe combined chloroform extracts were dried with magnesium sulfate
  3. customevaporated to an oil which
  4. customwas purified on a reverse phase HPLC C18 column
  5. washeluting with methanol/water (85:15) and 0.1% acetic acid
  6. customOn removal of the solvent 9.7 mg of the title compound
  7. customwas obtained as a colorless oil

Sources & evidence

ORD record
ord-db9d63eeb9094f4c8d76218e5c280479
Source dataset
uspto-grants-1995_10
Patent number
US05462954

Reaction notes

Loading…