Hydrochloric Acid → HCID 86594508, compound

HRID 858202Notes

Reaction equation

HRID 858202 reaction equation
[CH2:1]1[S:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].C([Li])CCC.[CH3:13][C:14]1[CH:15]=[C:16]([C:20]2[O:21][C:22]([CH3:36])=[C:23]([CH2:25][O:26][C@@H:27]3[CH2:32][CH2:31][CH2:30][C@H:29]([CH2:33][CH:34]=[O:35])[CH2:28]3)[N:24]=2)[CH:17]=[CH:18][CH:19]=1.Cl>O1CCCC1.CCCCCC>[OH:35][CH:34]([CH:1]1[S:7][C:5](=[O:6])[NH:4][C:2]1=[O:3])[CH2:33][C@H:29]1[CH2:30][CH2:31][CH2:32][C@@H:27]([O:26][CH2:25][C:23]2[N:24]=[C:20]([C:16]3[CH:15]=[C:14]([CH3:13])[CH:19]=[CH:18][CH:17]=3)[O:21][C:22]=2[CH3:36])[CH2:28]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5437ThiazolidinedioneHCID 86594507HCID 86594507, compoundHCID 178418339Butyllithium

Product 1

HCID 86594508HCID 86594508, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

214 mg of thiazolidinedione are dissolved in 20 ml of tetrahydrofuran and, at −78° C., 1.4 ml of a 2.7 M solution of n-butyllithium in n-hexane are added. The mixture is stirred at −78° C. for 30 minutes, and 500 mg of {cis-3-[2-(3-methylphenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl}acetaldehyde, dissolved in 10 ml of tetrahydrofuran, are then added. After 30 minutes of stirring at −78° C., the mixture is allowed to warm to room temperature. 20 ml of 1N hydrochloric acid are added and the mixture is extracted three times with in each case 50 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate and the solvent is then removed under reduced pressure. The residue is purified by RP-HPLC. This gives 420 mg of 5-{1-hydroxy-2-[cis-3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyl]ethyl}thiazolidine-2,4-dione as a white solid. C23H28N2O5S (444.45), MS (ESI): 445 (M+H+)

Workup

  1. additionare then added
  2. stirringAfter 30 minutes of stirring at −78° C.
  3. temperatureto warm to room temperature
  4. extractionthe mixture is extracted three times with in each case 50 ml of ethyl acetate
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. customthe solvent is then removed under reduced pressure
  7. customThe residue is purified by RP-HPLC

Sources & evidence

ORD record
ord-ca23bcad768341e9b563102ca9875af7
Source dataset
uspto-grants-2006_12
Patent number
US07148246B2

Reaction notes

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