P-Cresol → HCID 86613964, compound

HRID 1811461Notes

Reaction equation

HRID 1811461 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[C:10]([CH2:15][CH:16]3[S:20][C:19](=[O:21])[N:18](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:17]3=[O:41])[CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:42].[CH:43]1[C:48](O)=[CH:47][CH:46]=[C:45]([CH3:50])[CH:44]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(N=NC(OCC)=O)=O>C(OCC)(=O)C.C1COCC1>[CH3:50][C:45]1[CH:46]=[CH:47][C:48]([O:1][CH2:2][CH2:3][CH2:4][N:5]2[C:14]3[C:9](=[C:10]([CH2:15][CH:16]4[S:20][C:19](=[O:21])[NH:18][C:17]4=[O:41])[CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7][C:6]2=[O:42])=[CH:43][CH:44]=1

Participants

7

Reactant 4

HCID 2879P-CresolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86613962HCID 86613962, compound

Product 1

HCID 86613964HCID 86613964, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A THF solution (2 ml) of 100 mg (0.18 mmol) of 5-[1-(3-hydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]-3-trityl thiazolidine-2,4-dione, 0.0363 ml (0.347 mmol) of p-cresol, and 91.1 mg (0.35 mmol) of triphenylphosphine was cooled with ice. 0.158 ml of azodicarboxylic acid diethyl (2.2 M toluene solution) was added to the solution in an argon atmosphere. The mixture was stirred at room temperature for two hours, and ethyl acetate was added to the reaction liquid. After washing with water, the organic layer was concentrated under reduced pressure, and the residue was purified by preparative silica gel thin layer chromatography (n-hexane:ethyl acetate=1:1). The purified product was concentrated under reduced pressure, and 2 ml of a solution of 4N-hydrogen chloride/ethyl acetate was added to the residue. The mixture was stirred at room temperature overnight, and further stirred at 70° C. for 1.5 hours. The mixture was concentrated under reduced pressure, and the residue was purified by preparative silica gel thin layer chromatography (n-hexane:ethyl acetate=1:1). The purified product was concentrated under reduced pressure and evaporated to dryness, giving 27.1 mg (34.4% yield) of 5-{1-[3-(4-methylphenoxy)propyl]-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl}thiazolidine-2,4-dione as a colorless amorphous solid.

Workup

  1. washAfter washing with water
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customthe residue was purified by preparative silica gel thin layer chromatography (n-hexane:ethyl acetate=1:1)
  4. concentrationThe purified product was concentrated under reduced pressure, and 2 ml of a solution of 4N-hydrogen chloride/ethyl acetate
  5. additionwas added to the residue
  6. stirringThe mixture was stirred at room temperature overnight
  7. stirringfurther stirred at 70° C. for 1.5 hours
  8. concentrationThe mixture was concentrated under reduced pressure
  9. customthe residue was purified by preparative silica gel thin layer chromatography (n-hexane:ethyl acetate=1:1)
  10. concentrationThe purified product was concentrated under reduced pressure
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-2701e69419c64613b80d208d707d0701
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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